3-(Bromomethyl)-5-chloro-1-benzothiophene → HCID 57941416, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and 3-(bromomethyl)-5-chlorobenzo[b]thiophene (Maybridge plc, Tintagel, Cornwall, UK; 164 mg, 0.63 mmol) in dimethylformamide (5 mL) was heated at 100° C. for 2 days. The solvent was evaporated and ethyl acetate (50 mL) was added. The solution was washed with water (twice) and brine, dried (magnesium sulfate), filtered, evaporated and purified by chromatography, eluting with 1-3% methanol/dichloromethane to give (4S,7R)-2-(5-chloro-benzo[b]thiophen-3-ylmethyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (140 mg, 74%) as an off-white foam. APCI(+)-MS (M+H) 387.

Provenance & Evidence