Acetone → 3-ethylsulfonyl-N-methyl-N-(4-trifluoromethoxyphenyl)picolinamide
Reaction equation
CI.[CH2:3]([S:5]([C:8]1[C:9]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])[CH3:4].[C:28](=O)([O-])[O-].[K+].[K+].CC(C)=O>O.CN(C=O)C>[CH2:3]([S:5]([C:8]1[C:9]([C:14]([N:16]([CH3:28])[C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[CH:19][CH:18]=2)=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
0.50 g of methyl iodide was added to a mixture of 0.20 g of 3-ethylsulfonyl-N-(4-trifluoromethoxyphenyl)picolinamide (Compound of Present Invention 21), 0.12 g of potassium carbonate and 3 mL of acetone, and the mixture was stirred at room temperature for 1 hour. 1 mL of DMF was added to the reaction mixture, and the mixture was stirred at 60° C. for 2 hours. Water was poured to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.19 g of 3-ethylsulfonyl-N-methyl-N-(4-trifluoromethoxyphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 39).
Workup
- stirringthe mixture was stirred at 60° C. for 2 hours
- temperaturecooled to room temperature
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-78b3446fff6849148c8aab41da674e94
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09185910B2
Reaction notes
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