Potassium Carbonate → 6-Cyclohexylsulfanyl-pyridine-2-carboxylic acid methyl ester

HRID 62872

Reaction equation

HRID 62872 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[N:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH:18]1([SH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:24][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15290CyclohexanethiolHCID 16217886Methyl 6-bromopyridine-2-carboxylate

Product 1

HCID 901182516-Cyclohexylsulfanyl-pyridine-2-carboxylic acid methyl esterYield 46.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

After 6-bromo-pyridine-2-carboxylic acid methyl ester (0.30 g, 1.39 mmol) was dissolved in DMF (4 mL), K2CO3(0.575 g, 4.16 mmol) and cyclohexanethiol (0.25 mL, 2.08 mmol) were added thereto in turn, and the mixture was stirred at 70° C. for 18 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, extracted with EtOAc, and purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (0.162 g, 46%).

Workup

  1. customAfter the termination of the reaction
  2. concentrationthe reactant was concentrated under reduced pressure
  3. extractionextracted with EtOAc
  4. custompurified by column chromatography (eluent, EtOAc/Hex=1/5)

Sources & evidence

ORD record
ord-5de57498ae4f48acbce22a701ea55cc6
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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