反应详情

温度

-78 °C

In a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 6-bromo-4-chloro-3-phenylquinoline (460 mg, 1.44 mmol, Intermediate 3, step c), (4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanone (266 mg, 1.21 mmol, Intermediate 18, step b) in tetrahydrofuran (20 mL). This solution was cooled to −78° C., followed by the addition of n-BuLi (0.624 mL, 1.56 mmol, 2.5M in hexane) dropwise. The mixture was gradually warmed to room temperature. After 4 hours stirring, 1.0 M HCl was added until pH 6-7. After removal of solvent under vacuum, the residue was purified by flash column chromatography (silica gel column, 100:0˜15:1 EtOAc/petroleum ether) to give the title compound as a white solid. 1H NMR (300 MHz, MeOH-d4) δ=8.83 (s, 1H), 8.39 (d, J=1.5 Hz, 1H), 8.12 (d, J=9.0 Hz, 1H), 7.88 (dd, J=1.9, 8.9 Hz, 1H), 7.75 (s, 1H), 7.46-7.62 (m, 5H), 7.41 (s, 4H), 6.35 (s, 1H), 3.51 (s, 3H); MS m/e 460 [M+H]+.

1. customIn a 100-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. temperatureThe mixture was gradually warmed to room temperature
4. customAfter removal of solvent under vacuum
5. customthe residue was purified by flash column chromatography (silica gel column, 100:0˜15:1 EtOAc/petroleum ether)