Hydrochloric Acid → (4-Chloro-3-phenylquinolin-6-yl)(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence