Potassium Carbonate → 2-(4-Pyridylmethylthio)-N-(4-trifluoromethylsulfonylphenyl)pyridine-3-carboxamide
Reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][SH:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1[C:22]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([C:35]([F:38])([F:37])[F:36])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=1>C(O)C.C(OCC)(=O)C>[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9][C:17]2[C:22]([C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([S:32]([C:35]([F:38])([F:36])[F:37])(=[O:34])=[O:33])=[CH:30][CH:31]=3)=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
4-Pyridinemethanethiol hydrochloride (0.32 g, 2.0 mmol) and potassium carbonate (0.63 g, 4.5 mmol) were added to a solution of 2-chloro-N-(4-trifluoromethylsulfonylphenyl)pyridine-3-carboxamide (0.65 g, 1.8 mmol, Reference compound No. 2-2) in ethanol (10 mL) under a nitrogen atmosphere, then the mixture was stirred at 65° C. for 8 hours. The reaction mixture was diluted with ethyl acetate (100 mL), then the ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (100 mL) and brine (100 mL), and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, then the resulting residue was purified by silica gel column chromatography to give 0.29 g of the target compound as a white solid. (Yield 37%)
Workup
- washthe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (100 mL) and brine (100 mL)
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-74a12cae3de74ae7974bcaa3635d7a5a
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518973B2
Reaction notes
Loading…