73895-98-4

Usage

Uses

Used in Organic Synthesis:
2-Bromoo-4-methyl-6-aminopyridine is used as a building block in organic synthesis for the preparation of various biologically active compounds. Its unique structure allows for the formation of diverse chemical entities with potential applications in different fields.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-Bromoo-4-methyl-6-aminopyridine is employed as a key intermediate for the synthesis of pharmaceuticals. Its presence in the molecular structure can influence the pharmacological properties of the final drug, contributing to its therapeutic effects.
Used in Agrochemical Synthesis:
2-Bromoo-4-methyl-6-aminopyridine is utilized in the synthesis of agrochemicals, where it serves as a crucial component in the development of pesticides and other agricultural products. Its incorporation can enhance the effectiveness of these chemicals in protecting crops and improving yield.
Used in Dye Synthesis:
2-Bromoo-4-methyl-6-aminopyridine is also used in the synthesis of dyes, where its structural features contribute to the color and properties of the resulting dye products. Its use in this industry aids in the creation of a wide range of dyes for various applications, including textiles, inks, and pigments.
Used in Chemical Research:
2-Bromoo-4-methyl-6-aminopyridine is a valuable tool in chemical research, where it is employed to study various chemical reactions and mechanisms. Its unique structure and properties make it an important compound for understanding and advancing the field of chemistry.

InChI:InChI=1/C6H7BrN2/c1-4-2-5(7)9-6(8)3-4/h2-3H,1H3,(H2,8,9)

Synthetic route

1,3-dicyano-2-methyl-2-hydroxypropane (72060-94-7) → 6-bromo-4-methylpyridine-2-amine (73895-98-4)

Conditions	Yield
With sodium hydroxide; hydrogen bromide In acetic acid; ethyl acetate	66%
With hydrogen bromide; acetic acid at 20℃; for 2h;

2-chloromethyl-2-methyloxiran (598-09-4) + 1,3-dicyano-2-methyl-2-hydroxypropane (72060-94-7) → 6-bromo-4-methylpyridine-2-amine (73895-98-4)

Conditions	Yield
With sodium hydroxide; hydrogen bromide In hydrogenchloride; water; acetic acid; ethyl acetate

acetic anhydride (108-24-7) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → N-(6-bromo-4-methyl-pyridin-2-yl)-acetamide (263894-96-8)

Conditions	Yield
With pyridine; dmap	89%

6-bromo-4-methylpyridine-2-amine (73895-98-4) + p-methoxybenzyl chloride (824-94-2) → 6-bromo-N,N-bis[(4-methoxyphenyl)methyl]-4-methylpyridin-2-amine

Conditions	Yield
Stage #1: 6-bromo-4-methylpyridine-2-amine With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; for 1h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 25℃; for 2h;	87.5%

2-(4,4-difluorocyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1227068-84-9) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → 6-(4,4-difluorocyclohex-1-en-1-yl)-4-methylpyridin-2-amine

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 100℃; for 16h;	83%

6-bromo-4-methylpyridine-2-amine (73895-98-4) + 2,5-hexanedione (110-13-4) → 2-bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine (771530-89-3)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 150℃; for 1h; Microwave irradiation;	82%
With toluene-4-sulfonic acid In toluene for 1.5h; Paal-Knorr reaction; Heating;
With sodium acetate; acetic acid In toluene for 48h; Heating / reflux;

6-bromo-4-methylpyridine-2-amine (73895-98-4) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 5-bromo-7-methylimidazo[1,2-a]pyridine

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate	76%

para-xylene (106-42-3) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → 1-bromo-3,6,9-trimethylpyrido[1,2-a]benzimidazole (1644526-66-8)

Conditions	Yield
With [bis(acetoxy)iodo]benzene at 40℃; for 12h; regioselective reaction;	76%

di-tert-butyl dicarbonate (24424-99-5) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → tert-butyl (6-bromo-4-methylpyridin-2-yl)carbamate (1206249-13-9)

Conditions	Yield
With triethylamine In tert-butyl alcohol at 20℃; for 24h;	76%

2-chloroethanal (107-20-0) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → 5-bromo-7-methylimidazo[1,2-a]pyridine

Conditions	Yield
In ethanol for 20h; Reflux;	75%

cyclopropanecarboxylic acid chloride (4023-34-1) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → N-(6-bromo-4-methylpyridin-2-yl)cyclopropanecarboxamide

Conditions	Yield
With trimethylamine In dichloromethane at 0 - 20℃; for 2h;	73%

2-bromo-4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridine (1407500-74-6) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → 6-bromo-N-(4-(1-(4-memoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridin-2-yl)-4-methylpyridin-2-amine (1407500-73-5)

Conditions	Yield
With caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 0.5h; Inert atmosphere;	59%

(E)-6-methyl-2-(prop-1-en-1-yl)-1,3,6,2-dioxazaborocane-4,8-dione (1422023-40-2) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → (E)-4-methyl-6-(prop-1-enyl)pyridin-2-amine (1146620-39-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 150℃; for 1h; Microwave irradiation;	59%

(R)-methyl 1-hydroxy-1-(thiazol-2-yl)-2,3-dihydro-1H-indene-5-carboxylate (1609947-97-8) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → (R)-methyl 1-(5-(6-amino-4-methylpyridin-2-yl)thiazol-2-yl)-1-hydroxy-2,3-dihydro-1H-indene-5-carboxylate

Conditions	Yield
With palladium diacetate; cesium fluoride; catacxium A; Trimethylacetic acid In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	57%

sulfuric acid (7664-93-9) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → 2-bromo-4-methyl-6-hydroxypyridine

Conditions	Yield
With sodium nitrite In water	56%
With sodium nitrite In water	56%

methyl (5R)-5-hydroxy-5-(thiazol-2-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate (1407500-64-4) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → (R)-methyl 5-[5-(6-amino-4-methylpyridin-2-yl)-1,3-thiazol-2-yl]-5-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate (1407500-66-6)

Conditions	Yield
With palladium diacetate; cesium fluoride; catacxium A; Trimethylacetic acid In 1,4-dioxane at 110℃; for 15h; Inert atmosphere;	42.4%

4,6-dichloropyrimidine (1193-21-1) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → C10H8BrClN4 (1350268-27-7)

Conditions	Yield
With potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 130℃; for 1h; Microwave irradiation;	33%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → 6-(3,4-Dihydro-1H-isoquinolin-2-yl)-4-methyl-pyridin-2-yl-amine

Conditions	Yield
at 130℃;

6-bromo-4-methylpyridine-2-amine (73895-98-4) + (3,4-dihydronaphthalen-2-yl)boronic acid (521917-51-1) → 6-(3,4-Dihydro-naphthalen-2-yl)-4-methyl-pyridin-2-ylamine (521917-11-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 100℃; Suzuki coupling;

6-bromo-4-methylpyridine-2-amine (73895-98-4) → 2-(3-chloro-benzyloxy)-6-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-pyridine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: p-TsOH*H2O / toluene / 1.5 h / Heating 2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C 2.2: tetrahydrofuran / 12 h / Heating View Scheme

6-bromo-4-methylpyridine-2-amine (73895-98-4) → methyl trans-4-[(1R or 1S)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Reflux 2.1: bis(pinacol)diborane; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2.2: 2.5 h / 90 °C / Inert atmosphere View Scheme

6-bromo-4-methylpyridine-2-amine (73895-98-4) → trans-4-[(1R or 1S)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Reflux 2.1: bis(pinacol)diborane; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2.2: 2.5 h / 90 °C / Inert atmosphere 3.1: sodium hydroxide; water / methanol / 1 h / 15 - 65 °C 3.2: 1.5 h / 50 °C View Scheme

6-bromo-4-methylpyridine-2-amine (73895-98-4) → methyl trans-4-[(1R or 1S)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-fluoroethyl]cyclohexanecarboxylate

Conditions

Yield

Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Reflux 2.1: bis(pinacol)diborane; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2.2: 2.5 h / 90 °C / Inert atmosphere 3.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; ethanol / 0.25 h / 20 °C View Scheme

6-bromo-4-methylpyridine-2-amine (73895-98-4) → trans-4-[(1R or 1S)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-fluoroethyl]cyclohexanecarboxylic acid

Conditions

Yield

Multi-step reaction with 4 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Reflux 2.1: bis(pinacol)diborane; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2.2: 2.5 h / 90 °C / Inert atmosphere 3.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; ethanol / 0.25 h / 20 °C 4.1: sodium hydroxide; water / methanol / 0.33 h / 100 °C / Microwave irradiation 4.2: pH 3 - 4 View Scheme

6-bromo-4-methylpyridine-2-amine (73895-98-4) → trans-4-[(1R or 1S)-(3-bromo-6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylic acid

Conditions

Yield

Multi-step reaction with 4 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Reflux 2.1: bis(pinacol)diborane; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2.2: 2.5 h / 90 °C / Inert atmosphere 3.1: sodium hydroxide; water / methanol / 1 h / 15 - 65 °C 3.2: 1.5 h / 50 °C 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.08 h / 23 °C View Scheme

6-bromo-4-methylpyridine-2-amine (73895-98-4) → sodium trans-4-[(1R or 1S)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate

Conditions

Yield

Multi-step reaction with 4 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Reflux 2.1: bis(pinacol)diborane; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2.2: 2.5 h / 90 °C / Inert atmosphere 3.1: sodium hydroxide; water / methanol / 1 h / 15 - 65 °C 3.2: 1.5 h / 50 °C 4.1: sodium methylate / isopropyl alcohol; methanol / 1 h / 70 °C View Scheme

6-bromo-4-methylpyridine-2-amine (73895-98-4) → 2-hydroxyethyl trans-4-[(1R or 1S)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate

Conditions

Yield

Multi-step reaction with 4 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Reflux 2.1: bis(pinacol)diborane; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2.2: 2.5 h / 90 °C / Inert atmosphere 3.1: sodium hydroxide; water / methanol / 1 h / 15 - 65 °C 3.2: 1.5 h / 50 °C 4.1: di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 16 h / 20 °C 4.2: 0.5 h View Scheme

6-bromo-4-methylpyridine-2-amine (73895-98-4) → (1R or 1S)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3-bipyridin-6'-yl)-1-[trans-4-(hydroxymethyl)cyclohexyl]ethanol

Conditions

Yield

Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Reflux 2.1: bis(pinacol)diborane; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2.2: 2.5 h / 90 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 19 h / -78 - 20 °C View Scheme

2-chloro-4-(difluoromethyl)pyridine (1204296-03-6) + 6-bromo-4-methylpyridine-2-amine (73895-98-4) → 6-bromo-N-(4-(difluoromethyl)pyridine-2-yl)-4-methylpyridine-2-amine (1411772-41-2)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 2h; Reflux;
With potassium tert-butylate In tetrahydrofuran at 0℃; for 2h; Reflux;
With potassium tert-butylate In tetrahydrofuran at 0℃; for 2h; Reflux;

Upstream product

• 72060-94-7 1,3-dicyano-2-methyl-2-hydroxypropane 
• 598-09-4 2-chloromethyl-2-methyloxiran 

Downstream Products

• 1609978-81-5 14,14-dimethyl-3,12-dioxo-2,4,13-trioxa-11-azapentadec-1-yl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609977-15-2 ({[(6-aminohexyl)oxy]carbonyl}oxy)methyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate trifluoroacetate 
• 1609976-88-6 phenyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609978-79-1 trans-3-{[(benzyloxy)carbonyl]amino}cyclobutyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609976-87-5 trans-3-aminocyclobutyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609978-78-0 benzyl 2,3,4-tri-O-benzyl-6-O-({trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexyl}carbonyl)-D-glucopyranoside 
• 1609976-99-9 [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609976-85-3 (2S)-2,3-dihydroxypropyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609978-77-9 cis-4-[(tert-butoxycarbonyl)amino]cyclohexyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609976-84-2 cis-4-aminocyclohexyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609976-83-1 2-hydroxy-2-methylpropyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609978-90-6 2-hydroxyethyl trans-4-[(1R)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1609978-89-3 chloromethyl trans-4-[(1R)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 
• 1421930-35-9 trans-4-[(1R)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylic acid 

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