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3-Fluoro-2-iodotoluene is a chemical compound characterized by a benzene ring with a fluorine atom and an iodine atom substitution. It is recognized for its role as a versatile building block in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and materials. Additionally, it serves as an intermediate in the production of dyes, pigments, and other fine chemicals. Due to its potential toxicity and reactivity, it requires careful handling and adherence to safety precautions to prevent harm from ingestion, inhalation, or skin contact, as well as to minimize respiratory irritation.

883502-14-5

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883502-14-5 Usage

Uses

Used in Pharmaceutical Industry:
3-Fluoro-2-iodotoluene is used as a key building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to advancements in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Fluoro-2-iodotoluene is utilized as an intermediate in the production of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in pest control and crop protection, thereby supporting agricultural productivity.
Used in Material Science:
3-Fluoro-2-iodotoluene is employed as a component in the development of new materials with specialized properties. Its presence in these materials can influence characteristics such as stability, reactivity, or specific interactions, making it valuable in material science research and applications.
Used in Dye and Pigment Production:
As an intermediate in the production of dyes and pigments, 3-Fluoro-2-iodotoluene contributes to the creation of a wide range of colorants used in various industries, including textiles, plastics, and printing inks. Its role in these processes is essential for achieving desired color properties and performance.
Used in Fine Chemicals Industry:
3-Fluoro-2-iodotoluene is also utilized in the synthesis of other fine chemicals, where its unique structure and reactivity are leveraged to produce specialty chemicals for use in various applications, such as research, chemical analysis, or as components in other industrial processes.

Check Digit Verification of cas no

The CAS Registry Mumber 883502-14-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,8,3,5,0 and 2 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 883502-14:
(8*8)+(7*8)+(6*3)+(5*5)+(4*0)+(3*2)+(2*1)+(1*4)=175
175 % 10 = 5
So 883502-14-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H6FI/c1-5-3-2-4-6(8)7(5)9/h2-4H,1H3

883502-14-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Fluoro-2-iodo-3-methylbenzene

1.2 Other means of identification

Product number -
Other names 1-fluoro-2-iodo-3-methylbenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:883502-14-5 SDS

883502-14-5Synthetic route

2-fluoro-6-methylaniline
443-89-0

2-fluoro-6-methylaniline

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

Conditions
ConditionsYield
Stage #1: 2-fluoro-6-methylaniline With hydrogenchloride In water at 0℃; for 0.25h;
Stage #2: With sodium nitrite In water at 0℃; for 1.67h;
Stage #3: With potassium iodide In water at 0℃; for 2.17h;
73%
NH-pyrazole
288-13-1

NH-pyrazole

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

1-(2-iodo-3-methylphenyl)-1H-pyrazole

1-(2-iodo-3-methylphenyl)-1H-pyrazole

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 2h; Microwave irradiation; Inert atmosphere; Schlenk technique;70%
benzimidazole
271-44-3

benzimidazole

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

1-(2-iodo-3-methylphenyl)-1H-indazole

1-(2-iodo-3-methylphenyl)-1H-indazole

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 2h; Microwave irradiation; Inert atmosphere; Schlenk technique;48%
1,2,4-Triazole
288-88-0

1,2,4-Triazole

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

1-(2-iodo-3-methylphenyl)-1H-1,2,4-triazole

1-(2-iodo-3-methylphenyl)-1H-1,2,4-triazole

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 6h; Microwave irradiation; Inert atmosphere; Schlenk technique;31%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

1-(2-iodo-3-methylphenyl)-1H-benzo[d][1,2,3]triazole

1-(2-iodo-3-methylphenyl)-1H-benzo[d][1,2,3]triazole

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 5h; Sealed tube; Inert atmosphere; Schlenk technique;19%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

2-fluoro-6-methyl-benzonitrile
198633-76-0

2-fluoro-6-methyl-benzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide at 80℃; for 16h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide at 80℃; for 16h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0) In dimethyl amine at 80℃; Inert atmosphere;
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

3-bromo-6-fluoro-2-methyl-benzonitrile
1255207-47-6

3-bromo-6-fluoro-2-methyl-benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

3-ethenyl-6-fluoro-2-methylbenzonitrile
1255207-48-7

3-ethenyl-6-fluoro-2-methylbenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

6-fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile
1255207-46-5

6-fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

tert-butyl (3S)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate
1426071-25-1

tert-butyl (3S)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
View Scheme
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
View Scheme
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

tert-butyl (3R,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
1426072-82-3

tert-butyl (3R,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 16 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
8: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

tert-butyl (3S,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
1426071-26-2

tert-butyl (3S,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 16 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
8: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

3-(2-bromo-acetyl)-6-fluoro-2-methyl-benzonitrile
1426073-08-6

3-(2-bromo-acetyl)-6-fluoro-2-methyl-benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 20 - 100 °C
3.2: 0.75 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: bis(triphenylphosphine)palladium(II) dichloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.75 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide; trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

C12H12FNO

C12H12FNO

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3R,9aS)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-3-hydroxy-hexahydro-pyrazino[2,1-c][ 1,4]oxazine-8-carboxylic acid tert-butyl ester
1426073-09-7

(3R,9aS)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-3-hydroxy-hexahydro-pyrazino[2,1-c][ 1,4]oxazine-8-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
4.1: diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
4.1: diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(S)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-6,7,9,9a-tetrahydro-1H-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester
1426073-10-0

(S)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-6,7,9,9a-tetrahydro-1H-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
4.1: diisopropylamine / tetrahydrofuran / 18 h / 20 °C
5.1: triethylamine / dichloromethane / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
4.1: diisopropylamine / tetrahydrofuran / 18 h / 20 °C
5.1: triethylamine / dichloromethane / 0.5 h / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

C21H28FN3O6S

C21H28FN3O6S

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

tert-butyl (3R)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxylethyl]-3-(hydroxymethyl)piperazine-1-carboxylate
1426071-27-3

tert-butyl (3R)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxylethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 1 h / 150 °C / Microwave irradiation
View Scheme
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5: ethanol / 1 h / 150 °C / Microwave irradiation
View Scheme
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 1 h / 150 °C / Microwave irradiation
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

A

tert-butyl (3S,9aR)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
1426072-83-4

tert-butyl (3S,9aR)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

B

tert-butyl (3R,9aR)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
1426072-84-5

tert-butyl (3R,9aR)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 12 h / 20 °C
6.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 1 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 100 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3S,9aR)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-3-hydroxy-hexahydro-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester
1426073-11-1

(3S,9aR)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-3-hydroxy-hexahydro-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: bis(triphenylphosphine)palladium(II) dichloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.75 h / 0 - 5 °C
4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide; trifluorormethanesulfonic acid / 1 h / 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5: 18 h / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3S)-benzyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate
1426071-28-4

(3S)-benzyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(7R,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate
1426072-85-6

(7R,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / toluene / 100 - 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(7S,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate
1426072-86-7

(7S,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / toluene / 100 - 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3R,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8-(9H,9aH)-dicarboxylate
1426071-29-5

(3R,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8-(9H,9aH)-dicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino [1,2-a]pyrazine-2(6H)-carboxylate
1426071-30-8

(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino [1,2-a]pyrazine-2(6H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3S,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8 (9H,9aH)-dicarboxylate
1426071-31-9

(3S,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8 (9H,9aH)-dicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / toluene / 100 - 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide; trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 34 °C
8.2: 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a ]pyrazine-2(6H)-carboxylate
1426071-32-0

(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a ]pyrazine-2(6H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / toluene / 100 - 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide; trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 34 °C
8.2: 20 °C
9.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

6-fluoro-2-methyl-3-[(3S,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile 2,2,2-trifluoroacetate
1426072-49-2

6-fluoro-2-methyl-3-[(3S,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile 2,2,2-trifluoroacetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
7.1: 1 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
7.1: 1 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 16 h / 100 °C / Inert atmosphere
7: 1 h / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

3-((3S,9aS)-8-(2-(5-(1H-tetrazol-1-yl)pyridin-2-yl)acetyl)octahydropyrazino[2,1-c][1,4]oxazin-3-yl)-6-fluoro-2-methylbenzonitrile
1443735-03-2

3-((3S,9aS)-8-(2-(5-(1H-tetrazol-1-yl)pyridin-2-yl)acetyl)octahydropyrazino[2,1-c][1,4]oxazin-3-yl)-6-fluoro-2-methylbenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: triethylamine
7.1: ethyl acetate; hexane / 50 °C
8.1: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
9.1: 1 h / 20 °C
10.1: triethylamine / dichloromethane / 0.08 h
10.2: 2 h
View Scheme
Multi-step reaction with 10 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: triethylamine
7.1: ethyl acetate; hexane / 50 °C
8.1: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
9.1: 1 h / 20 °C
10.1: triethylamine / dichloromethane / 0.08 h
10.2: 2 h
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
7.1: 1 h / 20 °C
8.1: triethylamine / dichloromethane / 0.08 h
8.2: 2 h
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

6-fluoro-2-methyl-3-[(3S,9aS)-8-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile
1443735-04-3

6-fluoro-2-methyl-3-[(3S,9aS)-8-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
8: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
9: 1 h / 20 °C
10: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 4 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
8: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
9: 1 h / 20 °C
10: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 4 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
7.1: 1 h / 20 °C
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 4 h / 20 °C
View Scheme

883502-14-5Downstream Products

883502-14-5Relevant articles and documents

Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations

Boelke, Andreas,Nachtsheim, Boris J.

supporting information, p. 184 - 191 (2019/12/11)

The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the α-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements. (Figure presented.).

THERMOSETTING ALKOXYSILYL COMPOUND HAVING TWO OR MORE ALKOXYSILYL GROUPS, COMPOSITION AND CURED PRODUCT COMPRISING SAME, USE THEREOF, AND METHOD FOR PREPARING ALKOXYSILYL COMPOUND

-

, (2018/06/15)

The present invention relates to: a thermosetting alkoxysilyl compound (hereinafter, referred to as “alkoxysilyl compound”)having two or more alkoxysilyl groups showing excellent heat-resistance characteristics in a composite; a composition and a cured product comprising the same; a use thereof; and a method for preparing an alkoxysilyl compound. The composition of an alkoxysilyl compound, comprising a novel alkoxysilyl compound according to the present invention shows, in a composite, improved heat-resistance characteristics, i.e., an effect of decreasing the CTE of the composition of an alkoxysilyl compound and not showing a glass transition temperature (hereinafter, referred to as “Tg-less”). Further, the cured product comprising an alkoxysilyl compound according to the present invention shows excellent flame retardant properties due to the alkoxysilyl groups.

Bisphenol-based epoxy compound using thiol-ene reaction and method for preparing the same, and composite of organic-inorganic materials comprising a cured product thereof and method for preparing the composite

-

, (2017/08/24)

The present invention relates to a bisphenol-based epoxy compound having an alkoxysilylalkyl-S-alkyl group and a method for preparing the same, a composite of organic-inorganic materials comprising the cured product and a method for preparing the composite. The novel bisphenol-based epoxy compound can provide a composite which shows improved thermal resistance and thermal expansion properties and has excellent hardness when being used for manufacturing high-integration and high-performance electronic components such as a next-generation semiconductor substrate and PCB.COPYRIGHT KIPO 2017

METHOD OF CONSISTENTLY PRODUCING DIALLYLBISPHENOLS

-

Paragraph 0104-0107, (2017/01/23)

The purpose of the present invention is to provide a method of consistently producing high-quality diallylbisphenols with high yields from bisphenols. This method involves steps (1) through (3) below, and enables the consistent production of diallylbisphenols from bisphenols. (1) A step for reacting allyl halides and bisphenols or alkali metal salts thereof in a cellosolve solvent in the presence or absence of basic alkali metal salts, (2) a step for separating inorganic salt by-products from a reaction solution obtained in step (1), and (3) a step for heating and subjecting to a rearrangement reaction the reaction solution obtained in step (2).

ALKOXYSILYL COMPOUND HAVING AT LEAST TWO ALKOXYSILYL GROUPS, COMPOSITION, CURED PRODUCT THEREOF, USE THEREOF AND PREPARING METHOD OF ALKOXYSILYL COMPOUND HAVING AT LEAST TWO ALKOXYSILYL GROUPS

-

, (2016/12/07)

The present invention relates to an alkoxysilyl compound having two or more alkoxysilyl groups (hereinafter, referred to as ″alkoxysilyl compound″) showing an excellent heat-resistance in a composite, a composition and a cured product comprising the same, an use thereof, and a method for preparing the alkoxysilyl compound. The alkoxysilyl composition comprising the novel alkoxysilyl compound, according to the present invention, in a composite, shows improved heat-resistance, i.e., an effect of decreasing CTE of the alkoxysilyl composition, or an effect of increasing glass transition temperature or not showing glass transition temperature (hereinafter, referred to as ″Tg less″) by forming a chemical bond between the alkoxysilyl group and a filler (fibers and/or particles). Further, the cured product comprising the alkoxysilyl compound according to the present invention shows an excellent flame retardant property due to the alkoxysilyl group. Moreover, when the alkoxysilyl composition according to the present invention is applied to a metal film of a substrate, an excellent adhesion to the metal film is exhibited due to a chemical bond between a functional group on a surface of the metal film and the alkoxysilyl group.

COMPOSITION AND CURED ARTICLE COMPRISING INORGANIC PARTICLES AND EPOXY COMPOUND HAVING ALKOXYSILYL GROUP, USE FOR SAME, AND PRODUCTION METHOD FOR EPOXY COMPOUND HAVING ALKOXYSILYL GROUP

-

Page/Page column, (2015/06/03)

There is provided a composition including an alkoxysilylated epoxy compound, a composition of which exhibits good heat resistance properties, low CTE and high glass transition temperature or Tg-less and not requiring a separate coupling agent, and inorganic particles, a cured product formed of the composition, and a use of the cured product. An epoxy composition including an alkoxysilylated epoxy compound and inorganic particles, an epoxy composition including an epoxy compound, inorganic particles and a curing agent, a cured product of the composition, and a use of the composition are provided. Since chemical bonds may be formed between the alkoxysilyl group and the inorganic particles and between the alkoxysilyl groups, a composition of the composition including the alkoxysilylated epoxy compound and the inorganic particles exhibits improved heat resistance properties, decreased CTE, and increased glass transition temperature or Tg less.

EPOXY COMPOUND HAVING ALKOXYSILYL GROUP, METHOD OF PREPARING THE SAME, COMPOSITION AND CURED PRODUCT COMPRISING THE SAME, AND USES THEREOF

-

, (2014/07/08)

Disclosed are an epoxy compound having an alkoxysilyl group, a composite of which exhibits good heat resistant properties and/or a cured product of which exhibits good flame retardant properties, a method of preparing the same, a composition comprising the same, and a cured product and a use of the composition. An alkoxysilylated epoxy compound comprising at least one of Chemical Formula S1 substituent and at least two epoxy groups in a core, a method of preparing the epoxy compound by an allylation, a claisen rearrangement, an epoxidation and an alkoxysilylation, an epoxy composition comprising the epoxy compound, and a cured product and a use of the composition are provided. The composite of the disclosed exhibits improved chemical bonding, good heat resistant properties, a low CTE, a high glass transition temperature or Tg-less The cured product of the composition exhibits good flame retardant properties.

Investigations of thiol-modified phenol derivatives for the use in thiol-ene photopolymerizations

Reinelt, Sebastian,Tabatabai, Monir,Fischer, Urs Karl,Moszner, Norbert,Utterodt, Andreas,Ritter, Helmut

, p. 1733 - 1740 (2014/08/18)

Thiol-ene photopolymerizations gain a growing interest in academic research. Coatings and dental restoratives are interesting applications for thiol-ene photopolymerizations due to their unique features. In most studies the relative flexible and hydrophilic ester derivative, namely pentaerythritoltetra(3-mercaptopropionate) (PETMP), is investigated as the thiol component. Thus, in the present study we are encouraged to investigate the performance of more hydrophobic ester-free thiol-modified bis-and trisphenol derivatives in thiol-ene photopolymerizations. For this, six different thiol-modified bis-and trisphenol derivatives exhibiting four to six thiol groups are synthesized via the radical addition of thioacetic acid to suitable allyl-modified precursors and subsequent hydrolysis. Compared to PETMP better flexural strength and modulus of elasticity are achievable in thiol-ene photopolymerizations employing 1,3,5-triallyl-1,3,5-triazine-2,4,6-trione (TATATO) as the ene derivative. Especially, after storage in water, the flexural strength and modulus of elasticity is twice as high compared to the PETMP reference system.

EPOXY COMPOUND HAVING ALKOXYSILYL GROUP, METHOD FOR PREPARING SAME, COMPOSITION AND CURED MATERIAL COMPRISING SAME, AND USAGE THEREOF

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, (2014/09/02)

Disclosed are an epoxy compound having an alkoxysilyl group, a composite of which exhibits good heat resistant properties and/or a cured product of which exhibits good flame retardant properties, a method of preparing the same, a composition comprising the same, a cured product of the composition and a use of the composition. An alkoxysilylated epoxy compound comprising at least one of Chemical Formula S1 substituent and at least two epoxy groups in a core, a method of preparing the epoxy compound by an allylation, a claisen rearrangement, a glycidylation and an alkoxysilylation, an epoxy composition comprising the epoxy compound, a cured product of the composition and a use of the composition are provided. The composite of the composition comprising the alkoxysilylated epoxy compound exhibits improved chemical bonding,-good heat resistant properties, a low CTE, a high glass transition temperature or Tg-less via the enhanced chemical bonding efficiency of alkoxysilyl group. The cured product of the composition exhibits good flame retardant properties.

Highly stable self-crosslinked anion conductive ionomers for fuel cell applications

Jasti, Amaranadh,Shahi, Vinod K.

, p. 19238 - 19241 (2014/05/20)

We report a simple method for the preparation of self-crosslinked anion conductive ionomers (SCL-ACIs) via polycondensation-Friedel-Crafts alkylation reactions without using any catalyst or crosslinking agent. The reported alkaline stable and methanol impervious SCL-ACIs with 2.45 mequiv. g -1 ion-exchange capacity (IEC) and 68 mS cm-1 hydroxide ion conductivity were assessed as suitable candidates for alkaline direct methanol fuel cell (ADMFC) applications. the Partner Organisations 2014.

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