Carbon Dioxide → HCID 86715656, compound

Participants

Reaction Steps

n-BuLi (2.66 M in hexanes, 0.883 mL, 2.35 mmol) was added dropwise to a stirred solution of 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.01 g, 2.35 mmol, Intermediate 47, step d) in THF (11.5 mL) under argon at ˜−70° C. After an additional 1 min, a pellet of dry ice (˜4 g, ˜90 mmol) was added to the dark solution, and the flask was quickly resealed, evacuated and flushed with argon. After another min, the resulting homogeneous yellow reaction was removed from the cold bath and stirred under ambient conditions for 5 min, and was then transferred to an ice bath and quenched with iodomethane (0.146 mL, 2.35 mmol) and DMSO (4.6 mL). The clear yellow reaction was stirred at 0° C. for 5 min, and was then rotovapped at rt to provide a thick light yellow slurry. This was treated with Li2CO3 (173 mg, 2.35 mmol) and iodomethane (0.438 mL, 7.03 mmol) and stirred at 40° C. for 30 min. The resulting opaque thin slurry was then diluted with DCM (15 mL), washed with water (2×25 mL), dried (Na2SO4), filtered, and concentrated to provide a white solid. This was recrystallized from hot heptane (10 mL), and the globular crystals were filtered and washed with heptane (2×6 mL) to provide the title compound as an off-white powder.

Provenance & Evidence