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3430-13-5

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3430-13-5 Usage

Description

It is an important intermediate in the organic synthesis, which has many applications, such as pharmaceutical intermediate, organic synthesis, organic solvent, production of dyes, pesticide, and spice. Specifically, this chemical can act as the raw material to prepare 2:2’-dipyridyl and its derivatives.1 Moreover, this compound may be involved in the synthesis of biaryls through a one-pot tandem borylation/Suzuki-Miyaura cross-coupling reaction catalyzed by a palladacycle.2 In addition, 5-bromo-2-methylpyridine has been demonstrated to function as the substrate in a general palladium-catalyzed coupling of aryl bromides/triflates and thiols.3 Besides, this substance can facilitate the synthesis of 5-arylamino-2-picolines via displacement of bromide by anthranilic acid and decarboxylation.4

Referrence

Willink, H. D. T.; Wibaut, J. P., The preparation of 2 : 2'-dipyridyl and some of its derivatives. Recueil Des Travaux Chimiques Des Pays-Bas 1935, 54, 275-283. Wang, L. H.; Cui, X. L.; Li, J. Y.; Wu, Y. S.; Zhu, Z. W.; Wu, Y. J., Synthesis of Biaryls through a One-Pot Tandem Borylation/Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by a Palladacycle. Eur. J. Org. Chem. 2012, 595-603. Itoh, T.; Mase, T., A general palladium-catalyzed coupling of aryl bromides/triflates and thiols. Org. Lett. 2004, 6, 4587-4590. Louis H. Peterson; Tolman, R. L., Reinvestigation of the synthesis of 5-arylamino-2-picolines J. Heterocycl. Chem. 1977.

Chemical Properties

Light yellow Cryst

Uses

5-Bromo-2-picoline is a halogenated pyridine derivative used is a building block in the preparation of nitrogen containing heterocyclic compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 3430-13-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,3 and 0 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3430-13:
(6*3)+(5*4)+(4*3)+(3*0)+(2*1)+(1*3)=55
55 % 10 = 5
So 3430-13-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H6BrN/c1-5-2-3-6(7)4-8-5/h2-4H,1H3

3430-13-5 Well-known Company Product Price

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  • Alfa Aesar

  • (H27085)  5-Bromo-2-methylpyridine, 98%   

  • 3430-13-5

  • 250mg

  • 1519.0CNY

  • Detail
  • Alfa Aesar

  • (H27085)  5-Bromo-2-methylpyridine, 98%   

  • 3430-13-5

  • 1g

  • 3293.0CNY

  • Detail
  • Aldrich

  • (17636)  5-Bromo-2-methylpyridine  ≥99.0% (HPLC)

  • 3430-13-5

  • 17636-250MG

  • 1,934.01CNY

  • Detail
  • Aldrich

  • (17636)  5-Bromo-2-methylpyridine  ≥99.0% (HPLC)

  • 3430-13-5

  • 17636-1G

  • CNY

  • Detail

3430-13-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Bromo-2-picoline

1.2 Other means of identification

Product number -
Other names 2-METHYL-5-BROMOPYRIDINE

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:3430-13-5 SDS

3430-13-5Synthetic route

5-Amino-2-methylpyridine
80287-53-2, 3430-14-6

5-Amino-2-methylpyridine

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
Stage #1: 5-Amino-2-methylpyridine With hydrogen bromide; bromine at -20 - -15℃; for 1.66667h;
Stage #2: With sodium nitrite In water at 20℃; for 1h;
Stage #3: With sodium hydroxide In water at -15 - 20℃; for 1h;
99%
Stage #1: 5-Amino-2-methylpyridine With hydrogen bromide; bromine In water at -20 - -15℃; for 1.66667h;
Stage #2: With sodium hydroxide; sodium nitrite In water at -25 - 20℃; for 1h; Time;
99%
With potassium nitrite; sulfuric acid anschliessend Behandeln mit Kupfer(I)-bromid;
5-bromo-2-pyridylacetic acid hydrochloride

5-bromo-2-pyridylacetic acid hydrochloride

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
at 180℃; under 33 Torr;61%
α-picoline
109-06-8

α-picoline

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
With aluminium trichloride; bromine at 100℃; for 2.5h;11%
With aluminum (III) chloride; bromine
picoline hydrochloride
14401-91-3

picoline hydrochloride

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
With bromine Erhitzen des Reaktionsprodukts auf 130grad;
α-picoline
109-06-8

α-picoline

A

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

B

3-bromo-2-picoline
38749-79-0

3-bromo-2-picoline

Conditions
ConditionsYield
With aluminium trichloride; bromine at 100℃; for 0.5h;A 14.4 g
B 9.5 g
With aluminium trichloride; bromine at 100℃; for 19h;A n/a
B 4.2 g
6-methylnicotinamide
6960-22-1

6-methylnicotinamide

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOCl; aqueous KOH
2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid
View Scheme
ethyl 6-methylnicotinate
21684-59-3

ethyl 6-methylnicotinate

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous NH3
2: NaOCl; aqueous KOH
3: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid
View Scheme
Multi-step reaction with 5 steps
1: N2H4+H2O
2: KNO2; aqueous HCl
4: aqueous KOH
5: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid
View Scheme
6-methylpyridine-3-carbohydrazide
197079-25-7

6-methylpyridine-3-carbohydrazide

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: KNO2; aqueous HCl
3: aqueous KOH
4: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid
View Scheme
6-methyl-nicotinoyl azide
64038-04-6

6-methyl-nicotinoyl azide

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: aqueous KOH
3: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid
View Scheme
(6-methyl-[3]pyridyl)-carbamic acid ethyl ester
247077-42-5

(6-methyl-[3]pyridyl)-carbamic acid ethyl ester

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous KOH
2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid
View Scheme
1,3-bis(6-methylpyridin-3-yl)urea
858844-85-6

1,3-bis(6-methylpyridin-3-yl)urea

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated aqueous HCl / 130 °C
2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid
View Scheme
5-Hydroxy-2-methylpyridine
1121-78-4

5-Hydroxy-2-methylpyridine

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

6-methylnicotinonitrile
3222-48-8

6-methylnicotinonitrile

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane Reflux;
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

5-bromo-2-methyl-pyridine-N-oxide
31181-64-3

5-bromo-2-methyl-pyridine-N-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 2h;100%
Stage #1: 5-bromo-2-methylpyridine With dihydrogen peroxide; acetic acid In dichloromethane at 50℃; for 18h;
Stage #2: With potassium carbonate In dichloromethane; water pH=9;
99%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 4h;99%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 16h; Suzuki Coupling;100%
With (C5H5FeC5H3C(CH3)NC6H4CH3)PdCl(tricyclohexylphosphine); potassium acetate In 1,4-dioxane at 100℃; for 6h; Suzuki coupling; Inert atmosphere;
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 16h;
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

3-iodo-6-methylpyridine
695-17-0

3-iodo-6-methylpyridine

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at -10℃; for 0.5h;
Stage #2: With iodine In tetrahydrofuran at 0℃; for 2h;
99.5%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

tert-butyl(trimethylsilyl)phosphine
67033-70-9

tert-butyl(trimethylsilyl)phosphine

tert-butyl(6-methyl-3-pyridyl)phosphine

tert-butyl(6-methyl-3-pyridyl)phosphine

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride at 100℃; for 20h;99%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

4-dibenzofurylboronic acid
100124-06-9

4-dibenzofurylboronic acid

5-(dibenzo[b,d]furan-4-yl)-2-methylpyridine
1062229-27-9

5-(dibenzo[b,d]furan-4-yl)-2-methylpyridine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere;99%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

6-aminomethylpyridine-3-carbonitrile
782428-98-2

6-aminomethylpyridine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylpyridine With iminodicarboxylic acid di-tert-butyl ester; sodium hydride In tetrahydrofuran at 5 - 20℃;
Stage #2: With hydrogenchloride In methanol at 0 - 20℃; for 3h;
97%
2,4-dimethylthiazole
541-58-2

2,4-dimethylthiazole

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

2,4-dimethyl-5-(6-methylpyridin-3-yl)thiazole

2,4-dimethyl-5-(6-methylpyridin-3-yl)thiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;97%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

3-fluorophenylboronic acid
768-35-4

3-fluorophenylboronic acid

5-(3-fluorophenyl)-2-methylpyridine
713143-67-0

5-(3-fluorophenyl)-2-methylpyridine

Conditions
ConditionsYield
With potassium phosphate; {2-[2-(di(2-naphthyloxy)phosphinoxy)-3,5-bis(tert-butyl)phenyl]-4,6-bis(tert-butyl)phenoxy}di(2-naphthyloxy)phosphine; (1,5-cyclo-octadiene) nickel complexes In toluene at 80℃; for 6h;96%
3,5-dimethyl-1,2-oxazole
300-87-8

3,5-dimethyl-1,2-oxazole

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

3,5-dimethyl-4-(6-methylpyridin-3-yl)isoxazol

3,5-dimethyl-4-(6-methylpyridin-3-yl)isoxazol

Conditions
ConditionsYield
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;96%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

2-methyl-5-(1-methyl-1H-imidazol-5-yl)pyridine

2-methyl-5-(1-methyl-1H-imidazol-5-yl)pyridine

Conditions
ConditionsYield
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;96%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

(E)-5-bromo-2-(4-chlorostyryl)pyridine

(E)-5-bromo-2-(4-chlorostyryl)pyridine

Conditions
ConditionsYield
With 1,10-phenanthroline-5,6-dione; trifluorormethanesulfonic acid; oxygen In chlorobenzene at 120℃; under 760.051 Torr; for 24h;96%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

benzophenone hydrazone
5350-57-2

benzophenone hydrazone

N-benzhydrylidene-N'-(6-methyl-pyridin-3-yl)-hydrazine
337533-94-5

N-benzhydrylidene-N'-(6-methyl-pyridin-3-yl)-hydrazine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate95%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

2-methyl-4-(6-methylpyridin-3-yl)but-3-yn-2-ol
52535-35-0

2-methyl-4-(6-methylpyridin-3-yl)but-3-yn-2-ol

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine at 60℃; for 6h;95%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

phenylmethanethiol
100-53-8

phenylmethanethiol

5-(benzylthio)-2-methylpyridine
907202-06-6

5-(benzylthio)-2-methylpyridine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 16h; Inert atmosphere;95%
With N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 110℃; for 3h;94%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

5-(1,2-dimethyl-1H-imidazol-5-yl)-2-methylpyridine

5-(1,2-dimethyl-1H-imidazol-5-yl)-2-methylpyridine

Conditions
ConditionsYield
With C68H64Cl3N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Reagent/catalyst; regioselective reaction;95%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

2-[3-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl}-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine
1380445-20-4

2-[3-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl}-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine

4,6-diphenyl-2-[3-(6-methylpyridin-3-yl)-5-(9-phenanthryl)phenyl]-1,3,5-triazine

4,6-diphenyl-2-[3-(6-methylpyridin-3-yl)-5-(9-phenanthryl)phenyl]-1,3,5-triazine

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; XPhos In 1,4-dioxane; water at 80℃; for 24h; Inert atmosphere;94%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

benzaldehyde
100-52-7

benzaldehyde

5-(α-hydroxybenzyl)-2-methylpyridine

5-(α-hydroxybenzyl)-2-methylpyridine

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at -10℃; for 0.5h;
Stage #2: benzaldehyde In tetrahydrofuran at 0℃; for 2h;
93%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

p-methoxybenzylmercaptan
6258-60-2

p-methoxybenzylmercaptan

5-(4-methoxybenzylsulfanyl)-2-methylpyridine

5-(4-methoxybenzylsulfanyl)-2-methylpyridine

Conditions
ConditionsYield
With C47H54OP2PdSi2; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 1h; Sealed tube; Inert atmosphere;92%
With N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 7h; Heating;85%
With N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 7h; Suzuki-Miyaura reaction; Heating / reflux;85%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

allyl bromide
106-95-6

allyl bromide

5-allyl-2-methyl-pyridine

5-allyl-2-methyl-pyridine

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at -10℃; for 0.5h;
Stage #2: allyl bromide In tetrahydrofuran at 0℃; for 2h;
92%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

phenylboronic acid
98-80-6

phenylboronic acid

5-phenyl-2-picoline
3256-88-0

5-phenyl-2-picoline

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 140℃; for 0.25h; Inert atmosphere; Microwave irradiation;92%
With 1-butyl-3-methylimidazolium hexafluorophosphate; palladium diacetate; sodium carbonate In water at 80℃; for 12h; Suzuki coupling; Inert atmosphere;86%
With potassium phosphate; [Pd2(3,4-dichloroacetophenone thiosemicarbazone)2(bis(diphenylphosphino)ferrocene)] In N,N-dimethyl-formamide at 130℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;73%
Conditions
ConditionsYield
With N4,N7-bis(2-hydroxyethyl)-1,10-phenanthroline-4,7-diamine; sodium L-ascorbate; potassium hydroxide; copper(I) bromide In water; N,N-dimethyl-formamide at 120℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;92%
2-methylfuran
534-22-5

2-methylfuran

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

2-methyl-5-(5-methylfuran-2-yl)pyridine

2-methyl-5-(5-methylfuran-2-yl)pyridine

Conditions
ConditionsYield
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; acetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;92%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

benzylamine
100-46-9

benzylamine

(E)-5-bromo-2-styrylpyridine

(E)-5-bromo-2-styrylpyridine

Conditions
ConditionsYield
With 1,10-phenanthroline-5,6-dione; trifluorormethanesulfonic acid; oxygen In chlorobenzene at 120℃; under 760.051 Torr; for 24h;92%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

2-isopropylbenzenethiol
6262-87-9

2-isopropylbenzenethiol

5-(2-isopropylphenylsulfanyl)-2-methylpyridine

5-(2-isopropylphenylsulfanyl)-2-methylpyridine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 6h; Heating;91%
With N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 6h; Suzuki-Miyaura reaction; Heating / reflux;91%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

6,6’-dimethyl-3,3’-bipyridine
85484-42-0

6,6’-dimethyl-3,3’-bipyridine

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride In dimethyl sulfoxide at 120℃; for 8h;91%
With tetrabutylammomium bromide; potassium carbonate; palladium diacetate In water; N,N-dimethyl-formamide; isopropyl alcohol for 48h; Heating;51%
Stage #1: 5-bromo-2-methylpyridine With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.0333333h; Inert atmosphere;
Stage #2: With isopropyl alcohol In water; N,N-dimethyl-formamide for 48h;
51%
4-Methylthiazole
693-95-8

4-Methylthiazole

5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

4-methyl-5-(6-methylpyridin-3-yl)thiazole

4-methyl-5-(6-methylpyridin-3-yl)thiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;91%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

(E)-5-bromo-2-(4-methoxystyryl)pyridine

(E)-5-bromo-2-(4-methoxystyryl)pyridine

Conditions
ConditionsYield
With 1,10-phenanthroline-5,6-dione; trifluorormethanesulfonic acid; oxygen In chlorobenzene at 120℃; under 760.051 Torr; for 24h;90%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

C6(2)H6BrN

C6(2)H6BrN

Conditions
ConditionsYield
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h;90%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

tetraisopropylothiuram disulphide
4136-91-8

tetraisopropylothiuram disulphide

diisopropyl-dithiocarbamic acid 6-methyl-pyridin-3-yl ester

diisopropyl-dithiocarbamic acid 6-methyl-pyridin-3-yl ester

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at -10℃; for 0.5h;
Stage #2: tetraisopropylothiuram disulphide In tetrahydrofuran at 0℃; for 2h;
89%

3430-13-5Relevant articles and documents

Synthesis of C-14 and C-13, H-2-labeled IKK inhibitor: [14C] and [13C4,D3]-N-(6-chloro-7-methoxy-9H-pyrido3,4- blindol-8-yl)-2-methyl-3-pyridinecarboxamide

Li, Yuexian,Plesescu, Mihaela,Prakash, Shimoga R.

, p. 789 - 799 (2006)

[14C]-N-(6-Chloro-7-methoxy-9H-pyrido [3,4-b]indol-8-yl)-2- methyl-3-pyridinecarboxamide (5B), an IKK inhibitor, was synthesized from [ 14C]-barium carbonate in two steps in an overall radiochemical yield of 41%. The intermediate, [carboxyl-14C]-2-methylnicotinic acid, was prepared by the lithiation and carbonation of 3-bromo-2-methylpyridine. [ 13C4,D3]-N-(6-chloro-7-methoxy-9H-pyrido[3,4-b] indol-8-yl)-2-methyl-3-pyridinecarboxamide (5C) was synthesized from [1,2,3,4-13C4]-ethyl acetoacetate and [D 4]-methanol in six steps in an overall yield of 2%. [ l3C4]-2-methylnicotic acid, was prepared by condensation of [13C4]-ethyl 3-aminocrotonate and acrolein, followed by hydrolysis with lithium hydroxide. Copyright

A 2 - bromo -4 - pyridylaldehyde preparation method (by machine translation)

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Paragraph 0017; 0019; 0020; 0024, (2019/05/28)

The invention belongs to the field of organic synthesis, in particular relates to a 2 - bromo - 4 - pyridylaldehyde preparation method, comprises the following steps: (1) 2 - bromo - 4 - methyl pyridine preparation: will be hydrobromic arranged in four bottle, added under mixing 2 - amino - 4 - methylpyridine, to be 2 - amino - 4 - methyl pyridine completely after dissolving, cooling to - 20 °C, slow [...], dropping process control temperature is - 20 °C - - 15 °C; dropped stirring for 90 - 120 min, then dropping sodium nitrite solution, after adding, the temperature to 20 °C, stirring 45 - 60 min and then cooling to - 20 °C - - 25 °C, sodium hydroxide solution, dropping process control temperature is lower than - 15 °C - - 10 °C; after adding, the temperature is raised to 20 °C and stirring 1 h, extraction, the combined organic phase, washing, drying, concentration; (2) 2 - bromo - 4 - pyridylaldehyde preparation. The beneficial effect of the invention is: mild reaction conditions, is easy to operate, after treatment is simple, and easy to enlarge production, is extremely suitable for industrial production; high yield, low prices of raw materials, the production cost is low. (by machine translation)

Complexes of 4- and 5-bromo derivatives of 2-(hydroxymethyl)pyridine with copper(II) and cobalt(II) salts. Synthesis and X-ray crystal structures

Hubrich, Michael,Peukert, Max,Seichter, Wilhelm,Weber, Edwin

body text, p. 1854 - 1862 (2010/07/04)

Four copper(II) complexes (1-4) and a cobalt(II) complex (5) derived from 4-bromo-2-(hydroxymethyl)pyridine (L1) or 5-bromo-2-hydroxymethyl)pyridine (L2) with Cu(NO3)2·3H2O, CuCl2·2H2O and CoCl2·6H2O have been synthesized and their respective crystal structures studied. They show specific influences owing to the different kind of metal cations and counter anions, the hydration as well as the different position of the bromine substitution on both the coordination of the complex unit and the network structure of the crystal lattice. The Cu(II) complexes of L1 are five-coordinate [Cu(L1)2NO3]NO3·H2O (1) and [Cu(L1)2Cl]Cl·H2O (2) species with distorted quadratic pyramidal and trigonal bipyramidal coordination geometries of the N2O3 and N2O2Cl donor atoms around the Cu(II), respectively. The Cu(II) complexes of L2 are six-coordinate [Cu(L2)2(NO3)2] (3) and [Cu(L2)2Cl(H2O)]Cl·H2O (4) species with distorted octahedral coordination geometries of the N4O2 and N2O3Cl donor atoms. A distorted octahedral coordination geometry of the N2O2Cl2 donor atoms is also found in the complex unit [Co(L2)2Cl2] of the Co(II) complex 5 but showing the oxygen atoms of the chelating ligand as well as the chloride ions in a cis-position. Depending on the complex, water molecules and chloride anions are shown to act as stabilizing components of the crystal structure. The comparative structural investigation includes also known structures of the bromine-free ligand analogue 2-(hydroxymethyl)pyridine, illustrating the basic implication of the bromine substitution, mostly perceptible in the different modes of crystal packing.

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