反应详情

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid (178 mg, 0.65 mmol), tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 1-acetyl-5-bromo-7-nitroindoline (185 mg, 0.65 mmol), 0.65 mL of 2M sodium carbonate and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. The mixture was cooled, diluted with ethyl acetate (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 (5% methanol/ethyl acetate eluent) to give 63 mg (22%) of the title compound a yellow solid. mp 235°-240°. FDMS: m/e=433. α[D]589 =+65.72 (c=0.99, chloroform).

1. customfitted with a reflux condenser
2. temperaturethe stirred mixture was heated at 80°, under nitrogen, for 24 h
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 (5% methanol/ethyl acetate eluent)