Tributylvinyltin → N-(2-Methoxy-5-methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide

Participants

Reaction Conditions

Reaction Steps

Five batches each consisting of a mixture of N-(2-methoxy-5-methylphenyl)-7-iodo-1-benzofuran-5-sulfonamide (443 mg, 1.0 mmol; Intermediate 57), tributyl(vinyl)tin (350 mg, 1.1 mmol) and bis(triphenylphosphine)palladium diacetate (15 mg, 0.02 mmol) in acetonitrile (3 mL) was heated in a Smith Creator microwave oven to 180° C. for 5 min. The combined reaction mixtures were filtered and concentrated to give 2.0 g of crystalline crude material that was put through a SiO2 column using EtOAc/hexane (gradient 5:95→25:75) as eluent giving 1.3 g (75%) of off-white crystalline product. 1H NMR (400 MHz, CDCl3) δ 2.26 (s, 3H), 3.53 (s, 3H), 5.56 (dd, 1H), 6.16 (dd, 1H), 6.57 (d, 1H), 6.79-6.98 (m, 4H), 7.38 (d, 1H), 7.71-7.74 (m, 2H), 7.94 (d, 1H); MS (ESI+) for C18H17NO4S m/z 344 (M+H)+.

Provenance & Evidence