Methyl iodide → 3-ethylsulfanyl-N-methyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide
Reaction equation
[H-].[Na+].[CH2:3]([S:5][C:6]1[C:7]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=2)=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:4].CI.[C:27](=O)(O)[O-].[Na+]>O.C1COCC1>[CH2:3]([S:5][C:6]1[C:7]([C:12]([N:14]([CH3:27])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][N:16]=2)=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
0.9 g of 60% sodium hydride (oil-based) was added to a mixture of 0.65 g of 3-ethylsulfanyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide (Compound of Present Invention 2) and 4 mL of THF under ice cooling, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was ice-cooled, 1.0 g of methyl iodide was added thereto, and then the mixture was stirred at 30° C. for 2 hours. Water and a saturated aqueous sodium bicarbonate solution were 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 0.27 g of 3-ethylsulfanyl-N-methyl-N-(5-trifluoromethyl-pyridin-2-yl) picolinamide (hereinafter, referred to as Compound of Present Invention 16).
Workup
- temperaturecooled
- stirringthe mixture was stirred at 30° 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-ca19e88f96e54d2f998c8040f00c323e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09185910B2
Reaction notes
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