4-Fluorobenzyl bromide → HCID 57941472, compound

Participants

Reaction Steps

A solution of (4R,7S)-2-(2,4-difluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 42; 152 mg, 0.5 mmol), tetrabutylammonium iodide (195 mg, 0.52 mmol) and 4-fluorobenzyl bromide (0.33 mL, 2.57 mmol) in dimethylformamide (1 mL) was heated at 100° C. in a sealed tube for 9 h. The solvent was evaporated and ethyl acetate was added. The solution was washed with 10% aqueous sodium thiosulfate and brine, dried (sodium sulfate), filtered, evaporated, and purified using an Analogix Intelliflash 280 system (Analogix, Inc. Burlington, Wis.) with a RS-12G silica gel column, eluting with 20-100% ethyl acetate/hexanes, to give (4R,7S)-2-(2,4-difluoro-phenyl)-1-(4-fluoro-benzyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (167 mg, 81%) as an off-white solid. ES(+)-MS (M+H) 395.

Provenance & Evidence