2-(Bromomethyl)-5-(trifluoromethyl)furan → HCID 57941315, 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 2-bromomethyl-5-trifluoromethyl-furan (144 mg, 0.63 mmol) in N,N-dimethylformamide (5 mL) was heated at 110° C. for 2 days. The reaction mixture was evaporated and the residue was dissolved in ethyl acetate (50 mL), washed with water (2×25 mL) and brine (25 mL), dried (magnesium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 2-3% methanol/dichloromethane to give (4S,7R)-1,7,8,8-tetramethyl-2-(5-trifluoromethyl-furan-2-ylmethyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (136 mg, 78%) as a white solid. APCI-MS (M+H) 355.

Provenance & Evidence