Tributylvinyltin → 1-[(2-Methoxy-5-methylphenyl)sulfonyl]-4-vinyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

4-bromo-1-[(2-methoxy-5-methylphenyl)sulfonyl]-1H-indole (518 mg, 1.36 mmol; Intermediate 6), tributyl(vinyl)stannane (0.438 mL, 1.50 mmol) and Pd(PPh3)2OAc2 (51 mg, 0.068 mmol) were mixed in dry toluene (8 mL) and stirred 17 h at 110° C. using a STEM block. The mixture was filtered and additional tributyl(vinyl)stannane (0.200 mL, 0.68 mmol) and Pd(PPh3)2OAc2 (30 mg, 0.040 mmol) were added with continuous stirring for 23 h. Same procedure was repeated once more (additional reagents) with continuous stirring 24 h gave full conversion. The mixture was filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (DCM/hexane 2:3). This gave the desired product (2.62 g, 59%) as an off white solid. MS (ESI+) for C18H17NO3S m/z 328 (M+H)+.

Provenance & Evidence