Carbon Dioxide → HCID 86715656, compound

Participants

Reaction Steps

n-BuLi (2.66 M in hexanes, 0.883 mL, 2.35 mmol) was added dropwise over 4 minutes to a stirred solution of 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.01 g, 2.35 mmol, Intermediate 12: step d) in THF (11.5 mL) under argon at ˜−70° C. After an additional minute, 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 minute, the resulting homogeneous yellow reaction was removed from the cold bath and stirred under ambient conditions for 5 minutes, 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 minutes, and was then concentrated to remove the THF at room temperature 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 minutes. The resulting opaque thin slurry was then diluted with DCM (15 mL), washed with water (2×25 mL), dried (Na2SO4), filtered, and concentrated to dryness to provide a white solid. This solid 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