Ethanol → 3-Methyl-7-(4-fluorophenylsulfonyl)-9-phenyl-1,2,4,5-tetrahydro-3-benzazepine

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Reaction Conditions

Reaction Steps

A mixture of 3-methyl-7-(4fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine (0.9 g, 2 mmol), phenylboronic acid (0.4 g, 3 mmol), potassium carbonate (1.6 g, 12 mmol), ethanol (6 ml), water (6 ml), and toluene (25 ml) was degassed, then tetrakis(triphenylphosphine)palladium (0) (100 mg) was added and the mixture heated at 60° C. for 18 h. After cooling the mixture was poured into water (50 ml) and extracted with more ethyl acetate (50 ml). The resulting organic layer washed with brine (100 ml), dried (MgSO4), and evaporated. Isolation using an SCX column and subsequent chromatography on silica eluting with 0 to 10% methanol in dichloromethane containing 0.1M ammonia, gave the title compound as a white foam (0.6 g). 1H NMR δ (d6-DMSO) 2.2 (3H, s), 2.5 (4H, m), 2.8 (2H, m), 3.1 (2H, m), 7.2 (2H, m), 7.4 (5H, m), 7.6 (1H, s), 7.8 (1H, s), and 8.1 (2H, m).

Provenance & Evidence