Tributylvinyltin → 1-[(4-Methylphenyl)sulfonyl]-4-vinyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

4-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indole (600 mg, 1.71 mmol; Intermediate 3), tributyl(vinyl)stannane (0.550 mL, 1.88 mmol) and Pd(PPh3)2OAc2 (32 mg, 0.043 mmol) were mixed in dry toluene (8 mL) and stirred 24 h at 110° C. using a STEM block, then rt. for 40 h. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (20% DCM in hexane-50% DCM in hexane). This afforded the title compound 390 mg, 77% as a colorless sticky oil. MS (ESI+) for C17H15NO2S m/z 298 (M+H)+.

Provenance & Evidence