Tributylstannane → N-Acetyl-5-methoxy-3,4,6-trimethylindoline

Participants

Reaction Conditions

Reaction Steps

A solution of N-allyl-4-acetamido-3-bromo-2,6-dimethylanisole (8, 1.1 g, 3.6 mmol) in dry toluene (237 mL) and tri-n-butylstannane (1.9 mL, 7.1 mmol) was placed in a round-bottom flask fitted with a reflux condenser and slowly warmed to 60° C. under a nitrogen atmosphere. A catalytic amount of azobisisobutyronitrile was added, and the resulting mixture was heated and stirred at 85° C. for 15 h. The cooled reaction mixture was washed sequentially with 1% aq. ammonia and brine, and dried (MgSO4). Removal of solvents gave a liquid which was further purified by flash column chromatography using sequentially hexane and 1:3 ethyl acetate:hexanes as eluents to yield the indoline 9 (790 mg, 95% yield) as a colorless liquid. Spectral data: 13C NMR: δ 11.9, 16.4, 20.5, 23.9, 33.9, 57.3, 59.8, 116.5, 126.3, 129.7, 133.9, 137.6, 153.1, 168.2; HRMS: calcd. for C14H20NO2 (M+H+) 234.1494, fnd. 234.1487.

Provenance & Evidence