6-Bromo-4-methoxy-1H-indole → 1H-Indole, 6-ethenyl-4-methoxy-

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-4-(methyloxy)-1H-indole (900 mg, 3.98 mmol) in 1,2-dimethoxyethane (20 mL) was added tributylvinyltin (1.74 mL, 5.96 mmol). The reaction mixture was degassed with argon and then treated with dichlorobis(tri-o-tolylphosphine)palladium (153 mg, 0.19 mmol). The mixture was heated at 90° C. for 65 hours. The mixture was filtered through a pad of celite, washed with ethyl acetate and then the filtrate concentrated in vacuo. The product was purified by silica gel chromatography eluting with 2-50% ethyl acetate in hexane to yield the title compound (D8), (781 mg).

Provenance & Evidence