Tributylvinyltin → 3-Methyl-1-(phenylsulfonyl)-4-vinyl-1H-indole

Participants

Reaction Steps

Tributyl(vinyl)stannane (0.400 mL, 1.37 mmol) and Pd(PPh3)2OAc2 (51 mg, 0.069 mmol) were added to 4-bromo-3-methyl-1-(phenylsulfonyl)-1H-indole (240 mg, 0.69 mmol; Intermediate 29) in dry MeCN (4 mL). The reaction mixture was irradiated with micro-waves at 180° C. for 720 s. The mixture was combined with earlier batches of this intermediate (followed this experimental and starting with 4-bromo-3-methyl-1-(phenylsulfonyl)-1H-indole, 50 and 310 mg; Intermediate 29), filtered and concentrated. Purification was performed by flash chromatography (30% hexane in DCM). This afforded the product (420 mg, 82%) as a white solid. MS (ESI+) for C17H15NO2S m/z 298 (M+H)+.

Provenance & Evidence