Ethanol → HCID 16116993, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-2-(2,4-difluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 14; 500 mg, 1.64 mmol), tetrabutylammonium iodide (605 mg, 1.64 mmol) and 2,4-difluorobenzyl bromide (840 μL, 6.54 mmol) in dimethylformamide (10 mL) was heated at 100° C. overnight. Dichloromethane (250 mL) was added and the solution was washed with water (3×100 mL), aqueous sodium thiosulfate (100 mL), and brine (100 mL). The solution was dried (magnesium sulfate), filtered, evaporated, and purified by column chromatography, eluting with 45-50% ethyl acetate/petroleum ether. Fractions homogeneous for the product were concentrated to give an oil which was co-evaporated with ethanol and then held under high vacuum to give (4S,7R)-1-(2,4-difluoro-benzyl)-2-(2,4-difluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (508 mg, 71%). APCI(+)-MS (M+H) 431.

Provenance & Evidence