反应详情

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (200 mg, 0.65 mmol), tetrakis triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 3,5-dimethylphenylboronic acid (117 mg, 0.78 mmol), 0.65 mL of 2M sodium carbonate solution, 1.5 mL of toluene, and 1 mL of methanol, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24h. The mixture was cooled, diluted with dichloromethane (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent), to give 186 mg (86%) of the title compound as a white solid. mp 129°-130°. FDMS: m/e =333. α[D]589 =+73.31 (c=1.00, chloroform).

1. customfitted with a reflux condenser
2. temperaturethe stirred mixture was heated at 80°, under nitrogen, for 24h
3. temperatureThe mixture was cooled
4. washwashed with brine (2×25 mL)
5. dry with materialThe combined organic extracts were dried over sodium sulfate
6. concentrationconcentrated
7. custompurified by silica gel chromatography (ethyl acetate eluent)