(4-Chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanone → (3-Benzyl-2,4-dichloroquinolin-6-yl)(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanol

Participants

Reaction Steps

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-benzyl-6-bromo-2,4-dichloroquinoline (500 mg, 1.36 mmol, Intermediate 2: step c) in tetrahydrofuran (10 mL). n-BuLi (0.6 mL, 2.5 M in hexanes) was then added at −78° C. The resulting solution was stirred for 1 hour at −78° C. (4-Chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanone (301 mg, 1.36 mmol, Intermediate 1: step b) was added to this solution. The resulting solution was allowed to react, with stirring, for an additional 8 hours at room temperature. The reaction was then quenched by the addition of 10 mL of water/ice. The resulting solution was extracted with 3×20 mL of ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by chromatography over a silica gel column with dichloromethane/methanol to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=8.20 (s, 1H), 8.01 (d, J=8.5 Hz, 1H), 7.69-7.79 (m, 2H), 7.44 (d, J=7.5 Hz, 2H), 7.25-7.37 (m, 4H), 7.14-7.25 (m, 4H), 6.20 (s, 1H), 4.47 (s, 2H), 3.31 (s, 3H); MS m/e 508 [M+H]+.

Provenance & Evidence