Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:18])([CH3:17])[C:13]([F:16])([F:15])[F:14])[CH:6]=[CH:5]2.[H-].[Na+].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[CH3:21][S:22]([O:18][C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[N:8]=1)([CH3:17])[C:13]([F:15])([F:14])[F:16])(=[O:24])=[O:23]Participants
Procedure
To a solution of 6-Bromo-quinolin-2-yl-1,1,1-trifluoropropan-2-ol (5.06 g, 15.8 mmol) in THF (50 ml) was added sodium hydride (1.26 g, 31.6 mmol) portionwise at 0° C. and the mixture was stirred at room temperature for 2 hour. A solution of methanesulfonyl chloride (3.62 g, 31.6 mmol) in THF (10 ml) was added there at 0°. Then the reaction mixture was stirred at room temperature for 2 hours. The mixture was quenched with saturated sodium bicarbonate aqueous solution, and the product was extracted with ethyl acetate which was dried over sodium sulfate. Then, filtration, evaporation, purification through silica gel column chromatography eluting with hexane/ethyl acetate (15:1 to 5:1) furnished the title compound (6.29 g, 84% yield) as a white solid. 1H NMR (300 MHz, CDCl3) ppm 2.45 (3H, s), 3.24 (3H, s), 7.81-7.86 (2H, m), 7.96-8.05 (2H, m), 8.17 (1H, d, J=8.8 Hz). MS (ESI): m/z 397, 399 (M+H)+.
Workup
- stirringThen the reaction mixture was stirred at room temperature for 2 hours
- customThe mixture was quenched with saturated sodium bicarbonate aqueous solution
- extractionthe product was extracted with ethyl acetate which
- dry with materialwas dried over sodium sulfate
- filtrationThen, filtration, evaporation, purification through silica gel column chromatography
- washeluting with hexane/ethyl acetate (15:1 to 5:1)
Sources & evidence
- ORD record
- ord-3079872587b24efdb9c524c09119438a
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08134004B2
Linked notes
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