Tri(butyl)vinyltin → N-(2-Methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide

Participants

Reaction Steps

7-Iodo-N-(2-methylphenyl)-1-benzofuran-5-sulfonamide (0.41 g, 1 mmol; Intermediate 58), tributylvinyltin (0.32 mL, 1.1 mmol), bis(triphenylphosphine)palladium diacetate (10 mg) and acetonitrile (3 mL) were heated under microwave irradiation to 180° C. for 5 min. The mixture was cooled, filtered and evaporated. The resulting oil was washed with hexane (2×50 mL), dissolved in diethyl ether (50 mL), filtered and evaporated to give the crude product which was crystallized from ethanol:water (3:1). Yield 0.19 g (61%) of an off white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.93 (s, 3H) 5.57 (dd, J=11.3, 1.0 Hz, 1H) 6.12 (dd, J=17.8, 1.0 Hz, 1H) 6.84-7.07 (m, 6H) 7.62 (d, J=1.8 Hz, 1H) 7.84 (d, J=1.8 Hz, 1H) 8.14 (d, J=2.3 Hz, 1H) 9.43 (s, 1H).

Provenance & Evidence