Potassium Carbonate → Ethyl 2-(2-(4-cyanophenyl)pyridin-3-ylthio)-2-methylpropanoate

HRID 45769

Reaction equation

HRID 45769 reaction equation
[SH:1][C:2]1[C:3]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.Br[C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([C:3]2[C:2]([S:1][C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:9][CH:10]=1)#[N:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 679970364-(3-Mercaptopyridin-2-yl)benzonitrile

Product 1

HCID 67997044Ethyl 2-(2-(4-cyanophenyl)pyridin-3-ylthio)-2-methylpropanoateYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-mercaptopyridin-2-yl)benzonitrile (0.18 g, 0.85 mmol), ethyl 2-bromo-2-methylpropanoate (0.195 g, 1 mmol), and K2CO3 (0.138 g, 1.0 mmol) in DMF (2 mL) was stirred at room temperature for 2 hours. After the reaction was completed, the reaction mixture was washed with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated and purified by chromatography to yield ethyl 2-(2-(4-cyanophenyl)pyridin-3-ylthio)-2-methylpropanoate (0.137 g, 49%).

Workup

  1. washthe reaction mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-1d95349b8f544a7686245041bc015ba9
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Linked notes

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