Ammonia → (1S)-1-(2-{[7-(4-Fluorophenyl)quinolin-3-yl]sulfonyl}phenyl)ethanol

참여 물질

반응 단계

Sodium 7-(4-fluorophenyl)quinoline-3-sulfinate (2.52 g, 8.15 mmol), (1S)-1-(2-iodophenyl)ethanol (2.18 g, 8.79 mmol) and copper(I) iodide (4.69 g, 24.6 mmol) were weighed into a 3-neck round-bottomed flask. A nitrogen atmosphere was established by evacuation and back-filling with nitrogen. Dimethyl sulfoxide (50 mL) was added and the flask placed in an oil bath at 110° C. The reaction mixture was stirred at this temperature for 1 hour. The cooled reaction mixture was poured into concentrated ammonia solution (250 mL) and extracted with ethyl acetate (2×250 ml). The extracts were washed with brine (250 mL), combined, dried (MgSO4) and evaporated to an off-white solid. Recrystallisation from methanol gave the title compound (1.37 g, 41%). 1H NMR (500 MHz, DMSO-d6) δ 9.16 (2H, s), 8.41 (1H, d, J 8.6 Hz), 8.39 (1H, s), 8.19 (1H, dd, J 1.0, 8.0 Hz), 8.15 (1H, dd, J 1.7, 8.5 Hz), 7.99-7.97 (2H, m), 7.84 (1H, dd, J 1.0, 7.8 Hz), 7.78 (1H, t, J 7.1 Hz), 7.62-7.58 (1H, m), 7.39 (2H, t, J 8.8 Hz), 5.52-5.46 (1H, m), 5.29 (1H, d, J 3.9 Hz), 1.20 (3H, d, J 6.2 Hz); m/z (ES+) 408 [MH+].

출처 및 근거