Ammonia → 9-bromo-8-fluoro-5,6-dihydro-4H-4,6-methanobenzo[3,4]cyclohepta[1,2-b]thiophene-2-carboxamide

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Reaction Conditions

Reaction Steps

A pressure tube containing a solution of ethyl 9-bromo-8-fluoro-5,6-dihydro-4H-4,6-methanobenzo[3,4]cyclohepta[1,2-b]thiophene-2-carboxylate (32 mg, 0.08 mmol) in methanolic ammonia (5 mL of 7.0M ammonia in methanol) was warmed to 45° C. for two weeks. Evaporation of the reaction mixture furnished the title compound (31 mg, 0.08 mmol, 100%) as a pale brown solid: 1H NMR (500 MHz, d4-methanol) delta 1.61-1.68 (m, 2H), 2.93-3.02 (m, 2H), 3.59 (td, J=7.33, 4.26 Hz, 1H), 3.67 (td, J=8.04, 3.78 Hz, 1H), 7.05 (d, J=9.46 Hz, 1H), 8.18 (d, J=6.94 Hz, 1H), 8.39 (s, 1H); M+1=352/354.

Provenance & Evidence