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75806-84-7

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75806-84-7 Usage

General Description

2-Bromo-3-chloro-5-(trifluoromethyl)pyridine is a chemical compound with the formula C6H2BrClF3N. It is a pyridine derivative that contains bromine, chlorine, and a trifluoromethyl group. 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine is commonly used in the pharmaceutical and agrochemical industries as an intermediate for the synthesis of various compounds. It has been found to exhibit pesticidal and herbicidal activities, making it a valuable building block for the development of new agricultural products. Additionally, it can also be used in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals due to its versatile reactivity and functionality. Its unique combination of functional groups and potential applications make 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine a valuable compound in the field of organic chemistry and chemical synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 75806-84-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,8,0 and 6 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 75806-84:
(7*7)+(6*5)+(5*8)+(4*0)+(3*6)+(2*8)+(1*4)=157
157 % 10 = 7
So 75806-84-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H5F7N2/c1-3-2-4(16-15-3)5(8,9)6(10,11)7(12,13)14/h2H,1H3,(H,15,16)

75806-84-7 Well-known Company Product Price

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  • TCI America

  • (B4603)  2-Bromo-3-chloro-5-(trifluoromethyl)pyridine  >96.0%(GC)

  • 75806-84-7

  • 1g

  • 390.00CNY

  • Detail
  • TCI America

  • (B4603)  2-Bromo-3-chloro-5-(trifluoromethyl)pyridine  >96.0%(GC)

  • 75806-84-7

  • 5g

  • 1,450.00CNY

  • Detail
  • Alfa Aesar

  • (H32055)  2-Bromo-3-chloro-5-(trifluoromethyl)pyridine, 97%   

  • 75806-84-7

  • 250mg

  • 833.0CNY

  • Detail
  • Alfa Aesar

  • (H32055)  2-Bromo-3-chloro-5-(trifluoromethyl)pyridine, 97%   

  • 75806-84-7

  • 1g

  • 1215.0CNY

  • Detail
  • Alfa Aesar

  • (H32055)  2-Bromo-3-chloro-5-(trifluoromethyl)pyridine, 97%   

  • 75806-84-7

  • 5g

  • 2552.0CNY

  • Detail
  • Alfa Aesar

  • (H32055)  2-Bromo-3-chloro-5-(trifluoromethyl)pyridine, 97%   

  • 75806-84-7

  • 10g

  • 4780.0CNY

  • Detail

75806-84-7SDS

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 2-Bromo-3-Chloro-5-(Trifluoromethyl)Pyridine

1.2 Other means of identification

Product number -
Other names 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine

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:75806-84-7 SDS

75806-84-7Synthetic route

2,3-dichloro-5-trifluoromethylpyridine
69045-84-7

2,3-dichloro-5-trifluoromethylpyridine

2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

Conditions
ConditionsYield
With trimethylsilyl bromide at 100℃; for 15h; Inert atmosphere;90%
3-chloro-2-hydroxy-5-(trifluoromethyl)pyridine
76041-71-9

3-chloro-2-hydroxy-5-(trifluoromethyl)pyridine

2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

Conditions
ConditionsYield
With phosphorus(V) oxybromide at 150℃; for 6h; Temperature;58%
6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen fluoride; sulfur tetrafluoride / 12 h / 100 °C / 1125.11 Torr / Autoclave
2: N-chloro-succinimide / N,N-dimethyl-formamide; 1-methyl-pyrrolidin-2-one / 8 h / 20 °C
3: phosphorus(V) oxybromide / 6 h / 150 °C
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]aniline
824953-11-9

2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]aniline

Conditions
ConditionsYield
With water; sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide for 16h;95%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

2-(trifluoromethyl)-N-vinylbenzamide
1450903-41-9

2-(trifluoromethyl)-N-vinylbenzamide

fluopyram
658066-35-4

fluopyram

Conditions
ConditionsYield
With Cyclohexanethiol; 10-phenyl-10H-phenothiazine; sodium formate In water; dimethyl sulfoxide at 23℃; for 16h; Irradiation; Inert atmosphere; Sealed tube; Cooling; regioselective reaction;93%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

lithium cyanide
788104-34-7, 25733-05-5

lithium cyanide

3-chloro-2-cyano-5-(trifluoromethyl)pyridine
80194-70-3

3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-3-chloro-5-(trifluoromethyl)pyridine With 4-pyrrolidin-1-ylpyridine In ethanol for 6h; Reflux; Large scale;
Stage #2: lithium cyanide In water; 1,2-dichloro-ethane at 80℃; for 2h; Large scale;
88.1%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

(1-(tert-butoxycarbonyl)azetidin-3-yl)zinc(II) iodide
206446-38-0

(1-(tert-butoxycarbonyl)azetidin-3-yl)zinc(II) iodide

C9H8ClF3N2

C9H8ClF3N2

Conditions
ConditionsYield
Stage #1: 2-bromo-3-chloro-5-(trifluoromethyl)pyridine; (1-(tert-butoxycarbonyl)azetidin-3-yl)zinc(II) iodide With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 18h;
Stage #2: With hydrogenchloride In methanol; water at 20℃; for 60h;
88%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

(7‐methyl‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐7‐yl)methanol
1263188-55-1

(7‐methyl‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐7‐yl)methanol

7-({[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}methyl)-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

7-({[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}methyl)-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2.33333h; Inert atmosphere;88%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

N-benzoylethyleneimine
13313-25-2

N-benzoylethyleneimine

N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl)benzamide

N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl)benzamide

Conditions
ConditionsYield
With Cyclohexanethiol; 10-phenyl-10H-phenothiazine; sodium formate In water; dimethyl sulfoxide at 23℃; for 16h; Irradiation; Inert atmosphere; Sealed tube; Cooling; regioselective reaction;82%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

4-(trifluoromethyl)-N-vinylbenzamide

4-(trifluoromethyl)-N-vinylbenzamide

N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl)-4-(trifluoromethyl)benzamide
659745-39-8

N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl)-4-(trifluoromethyl)benzamide

Conditions
ConditionsYield
With Cyclohexanethiol; 10-phenyl-10H-phenothiazine; sodium formate In water; dimethyl sulfoxide at 23℃; for 16h; Irradiation; Inert atmosphere; Sealed tube; Cooling; regioselective reaction;82%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

potassium vinyltrifluoroborate

potassium vinyltrifluoroborate

3-chloro-5-(trifluoromethyl)-2-vinylpyridine

3-chloro-5-(trifluoromethyl)-2-vinylpyridine

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In tetrahydrofuran at 80℃; for 24h; Reagent/catalyst; Temperature; Time; Solvent; Inert atmosphere;71%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

methyl 5-cyclopropyl-2-fluoro-4-((3-methylazetidin-3-yl)methoxy)benzoate hydrochloride

methyl 5-cyclopropyl-2-fluoro-4-((3-methylazetidin-3-yl)methoxy)benzoate hydrochloride

methyl 4-((1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-3-methylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate

methyl 4-((1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-3-methylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate

Conditions
ConditionsYield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 110℃; for 16h; Inert atmosphere; Sealed tube;70%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

allyltributylstanane
24850-33-7

allyltributylstanane

C9H7ClF3N

C9H7ClF3N

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 70℃; for 3h;67%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole
1173983-43-1

10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole

10-Chloro-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole
1173978-19-2

10-Chloro-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole

Conditions
ConditionsYield
With [2,2]bipyridinyl; caesium carbonate; copper(l) iodide In 1-methyl-pyrrolidin-2-one at 150℃; for 16h;43%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

3-(difluoromethyl)-N-(1-hydroxypropan-2-yl)-1-methyl-1H-pyrazole-4-carboxamide
1105713-22-1

3-(difluoromethyl)-N-(1-hydroxypropan-2-yl)-1-methyl-1H-pyrazole-4-carboxamide

3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(3-chloro-5-trifluoromethyl-pyridin-2-yloxy)-1-methyl-ethyl]amide
1105713-21-0

3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(3-chloro-5-trifluoromethyl-pyridin-2-yloxy)-1-methyl-ethyl]amide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 3h;34%
N-(2-iodophenyl)-2-(trifluoromethyl)benzamide
362694-31-3

N-(2-iodophenyl)-2-(trifluoromethyl)benzamide

2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]phenyl}-2-(trifluoromethyl)benzamide

N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]phenyl}-2-(trifluoromethyl)benzamide

Conditions
ConditionsYield
Stage #1: N-(2-iodophenyl)-2-(trifluoromethyl)benzamide With potassium acetate; bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide at 90℃; for 2h;
Stage #2: 2-bromo-3-chloro-5-(trifluoromethyl)pyridine With water; sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide at 20 - 90℃; for 16h;
13%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

copper(l) cyanide

copper(l) cyanide

ammonium hydroxide

ammonium hydroxide

3-chloro-2-cyano-5-(trifluoromethyl)pyridine
80194-70-3

3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions
ConditionsYield
In N-methyl-acetamide; diethyl ether
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

3-chloro-5-trifluoromethylpyridine-2-carboxylic acid
80194-68-9

3-chloro-5-trifluoromethylpyridine-2-carboxylic acid

Conditions
ConditionsYield
With n-butyllithium In diethyl ether; hexane; nitrogen; water
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

C15H9Cl2F6N

C15H9Cl2F6N

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2 / water; 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

C15H12Cl2F3N

C15H12Cl2F3N

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2 / water; 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512811-37-8

5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme
Multi-step reaction with 3 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2 / water; 1,4-dioxane / 20 °C / Inert atmosphere; Heating
3: palladium diacetate; ruphos; sodium t-butanolate / 1,4-dioxane / 22 h / 20 °C / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

A

5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512811-37-8

5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

B

C21H18ClF3N2
1512812-57-5

C21H18ClF3N2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; ruphos; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) / water; 1,4-dioxane / 22 h / 20 °C / Inert atmosphere; Heating
View Scheme
Multi-step reaction with 3 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2 / water; 1,4-dioxane / 20 °C / Inert atmosphere; Heating
3: palladium diacetate; ruphos; sodium t-butanolate / 1,4-dioxane / 22 h / 20 °C / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

5-(2-fluorophenyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512811-66-3

5-(2-fluorophenyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

1-(3-(3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepin-5-yl)phenyl)ethanone
1512811-73-2

1-(3-(3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepin-5-yl)phenyl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

5-(3,5-dimethoxyphenyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512811-79-8

5-(3,5-dimethoxyphenyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

4-(3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepin-5-yl)benzonitrile
1512811-85-6

4-(3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepin-5-yl)benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

7-methyl-5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512811-91-4

7-methyl-5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

7-methoxy-5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512811-96-9

7-methoxy-5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

7-fluoro-5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512812-02-0

7-fluoro-5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

5-(p-tolyl)-3,8-bis(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512812-07-5

5-(p-tolyl)-3,8-bis(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: potassium carbonate; [Rh(OH)(cod)]2; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); XPhos / water; 1,4-dioxane / 22 h / Inert atmosphere; Heating
View Scheme

75806-84-7Relevant articles and documents

A for the synthesis of anti-cancer auxiliary drug pyridine medical process for the preparation of intermediates

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Paragraph 0026, (2017/01/26)

The invention relates to the field of medical chemistry and discloses a method for synthesizing a pyridine medical intermediate, namely 2-bromo-3-chloro-5-trifluoromethyl pyridine, for synthesizing anti-cancer auxiliary medicines. The method comprises the following steps of: (1) reacting 6-hydroxynicotinic acid, hydrofluoric acid and sulfur tetrafluoride at the temperature of between 100 and 120DEG C and under the pressure of 0.1-0.3MPa, and adding water to obtain 2-hydroxy-5-trifluoromethyl pyridine; (2) reacting with N-chlorosuccinimide, and performing water precipitation to obtain 3-chloro-5-trifluoromethyl-2-hydroxypyridine; and (3) adding excessive phosphorus oxybromide, reacting at the temperature of between 145 and 160DEG C for 5 to 8 hours, cooling, violently stirring at the temperature of between -5 and 0DEG C, extracting, combining organic phases, drying, filtering, performing spin drying, and purifying by using a silica gel column. According to the method, raw materials are readily available, the cost is low, the method is suitable for industrial production and the yield exceeds 38 percent.

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