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1,3-dicyano-2-methyl-2-hydroxypropane
6-bromo-4-methylpyridine-2-amine
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
1,3-dicyano-2-methyl-2-hydroxypropane
6-bromo-4-methylpyridine-2-amine
Conditions | Yield |
---|---|
With sodium hydroxide; hydrogen bromide In hydrogenchloride; water; acetic acid; ethyl acetate |
acetic anhydride
6-bromo-4-methylpyridine-2-amine
N-(6-bromo-4-methyl-pyridin-2-yl)-acetamide
Conditions | Yield |
---|---|
With pyridine; dmap | 89% |
6-bromo-4-methylpyridine-2-amine
p-methoxybenzyl chloride
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
6-bromo-4-methylpyridine-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
2,5-hexanedione
2-bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine
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
Bromoacetaldehyde diethyl acetal
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; ethyl acetate | 76% |
para-xylene
6-bromo-4-methylpyridine-2-amine
1-bromo-3,6,9-trimethylpyrido[1,2-a]benzimidazole
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 40℃; for 12h; regioselective reaction; | 76% |
di-tert-butyl dicarbonate
6-bromo-4-methylpyridine-2-amine
tert-butyl (6-bromo-4-methylpyridin-2-yl)carbamate
Conditions | Yield |
---|---|
With triethylamine In tert-butyl alcohol at 20℃; for 24h; | 76% |
2-chloroethanal
6-bromo-4-methylpyridine-2-amine
Conditions | Yield |
---|---|
In ethanol for 20h; Reflux; | 75% |
cyclopropanecarboxylic acid chloride
6-bromo-4-methylpyridine-2-amine
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
6-bromo-4-methylpyridine-2-amine
6-bromo-N-(4-(1-(4-memoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridin-2-yl)-4-methylpyridin-2-amine
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
6-bromo-4-methylpyridine-2-amine
(E)-4-methyl-6-(prop-1-enyl)pyridin-2-amine
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
6-bromo-4-methylpyridine-2-amine
Conditions | Yield |
---|---|
With palladium diacetate; cesium fluoride; catacxium A; Trimethylacetic acid In 1,4-dioxane at 100℃; for 20h; Inert atmosphere; | 57% |
sulfuric acid
6-bromo-4-methylpyridine-2-amine
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
6-bromo-4-methylpyridine-2-amine
(R)-methyl 5-[5-(6-amino-4-methylpyridin-2-yl)-1,3-thiazol-2-yl]-5-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate
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
6-bromo-4-methylpyridine-2-amine
C10H8BrClN4
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
6-bromo-4-methylpyridine-2-amine
Conditions | Yield |
---|---|
at 130℃; |
6-bromo-4-methylpyridine-2-amine
(3,4-dihydronaphthalen-2-yl)boronic acid
6-(3,4-Dihydro-naphthalen-2-yl)-4-methyl-pyridin-2-ylamine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 100℃; Suzuki coupling; |
6-bromo-4-methylpyridine-2-amine
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
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
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
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
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
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
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
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
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
6-bromo-4-methylpyridine-2-amine
6-bromo-N-(4-(difluoromethyl)pyridine-2-yl)-4-methylpyridine-2-amine
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; |
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