(4-Fluorophenyl)(1-methyl-1H-imidazol-5-yl)methanone → (2,4-Dichloro-3-(3-fluorophenyl)-8-methylquinolin-6-yl)(4-fluorophenyl)(1-methyl-1H-imidazol-5-yl)methanol

A round bottom flask was charged with 6-bromo-2,4-dichloro-3-(3-fluorophenyl)-8-methylquinoline (1.00 g, 2.60 mmol, Intermediate 50, step c) and (4-fluorophenyl)(1-methyl-1H-imidazol-5-yl)methanone (583 mg, 2.86 mmol, Intermediate 49, step b) and was evacuated and re-filled with argon (three times). THF (20 mL) was added, and the solution was cooled in a dry ice acetone bath for 2 minutes. At this point the mixture began to turn cloudy and n-BuLi (1.6 M in hexane, 2.11 mL, 3.38 mmol), was added over about 1 minute. The mixture was stirred at −78° C. for 10 minutes, then in an ice water bath for 1 hour. The reaction was quenched by addition of saturated aqueous NH4Cl, diluted with water and extracted with EtOAc (3×). The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 30-60% acetone-DCM) to afford slightly impure title compound as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 8.09 (s, 1H), 7.60 (s, 1H), 7.44-7.55 (m, 1H), 7.30-7.39 (m, 3H), 7.15-7.23 (m, 1H), 7.01-7.12 (m, 4H), 6.40 (s, 1H), 4.00 (br. s., 1H), 3.40 (s, 3H), 2.74 (s, 3H). MS m/e 510.1 [M+H]+.