Dimethyl Sulfoxide → HCID 58368654, compound

Participants

Reaction Conditions

Reaction Steps

Dimethyl sulfoxide (0.038 mL, 0.54 mmol) was added to oxalyl chloride (0.0286 mL, 0.339 mmol) in methylene chloride (1.26 mL) at −78° C. After 10 minutes, [5-bromo-8-(3-fluorophenyl)quinolin-7-yl]methanol (0.075 g, 0.22 mmol) in methylene chloride (2.53 mL) was added and the resulting mixture was stirred at −78° C. for 30 minutes. Triethylamine (0.157 mL, 1.13 mmol) was then added and the mixture was stirred for 5 hours to room temperature. After quenching with water, the mixture was extracted with methylene chloride. The organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated to dryness. The resulting mixture was purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the desired product (49 mg, 66%). LCMS calculated for C16H10BrFNO (M+H)+: m/z=330.0; Found: 330.0.

Provenance & Evidence