Dimethyl Sulfoxide → 6-(2,3-Difluorophenyl)-5-fluoro-7,8-dihydro-5H-cyclohepta[b]pyridin-9(6H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (1.2 g, 9.5 mmol) in dichloromethane (15 mL) at −65° C. was added DMSO (0.85 mL, 12 mmol), and the mixture was stirred for 30 min. A solution of 5R,6S,9R and 5S,6R,9S)-6-(2,3-difluorophenyl)-5-fluoro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol (0.35 g, 1.9 mmol) in dichloromethane (3 mL) was added dropwise and the resulting solution was stirred at −65° C. for 30 min. After triethylamine (2.3 mL, 17 mmol) was added, the reaction mixture was gradually warmed to 23° C. over a period of 4 h, and then partitioned between water and dichloromethane. The organic layer was washed with water (3×), brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 50% ethyl acetate in petroleum ether to give the title compound as a racemic mixture. MS: m/z=292.2 (M+1).

Provenance & Evidence