反応式
[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]参加物
実験手順
To a solution of of 2-(6-bromoquinolin-2-yl)-1,1,1-trifluoropropan-2-ol (1.93 g, 6.03 mmol) in THF (20 ml) was added sodium hydride (241 mg, 7.23 mmol) portionwise at 0° C. and the mixture was stirred at room temperature for 1 hour. A solution of methanesulfonyl chloride (829 mg, 7.23 mmol) in THF (2 ml) was added at 0°. Then the reaction mixture was stirred at room temperature for 16 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 and purification through silica gel column chromatography, eluting with hexane/ethyl acetate (15:1 to 5:1), furnished the title compound (1.11 g, 46% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 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)+.
後処理
- stirringThen the reaction mixture was stirred at room temperature for 16 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 and purification through silica gel column chromatography
- washeluting with hexane/ethyl acetate (15:1 to 5:1)
出典と根拠
- ORDレコード
- ord-cc783c4763174603acb41eb320c33e09
- 出典データセット
- uspto-grants-2012_04
- 特許番号
- US08158650B2
関連ノート
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