Sodium hydride → 6-Bromoquinolin-2-yl-2,2,2-trifluoro-1-methylethyl methanesulfonate

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Reaktionsschritte

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)+.

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