反应详情

Add 1,3-dihydro-3-methyl-1-phenyl-2H-pyrrolo[2,3-b]-pyridin-2-one (H) (3.0 g, 0.013 mole) portionwise to sodium hydride (0.63 g of 60% NaH in oil, 0.015 mole, washed with hexane) in dry THF (35 mL) at 10° C. under a N2 atmosphere. Stir for 30 minutes at room temperature, and then recool to 10° C. Add N-fluoro-N-neopentyl-p-toluenesulfonamide (4.1 g, 0.015 mole) in dry THF (30 mL) dropwise over 10 minutes. Warm reaction mixture up to room temperature slowly, and stir for 16 hours. Pour onto ice/water (100 mL), and neutralize to pH=4 to 5 with 15% aqueous HCl. Separate layers. Dry organic solution with MgSO4, filter, and rotoevaporate to give an oil. Dissolve the oil in dichloromethane, and chromatograph on silica gel, eluting with 30% ethyl acetate-hexane. Combine the appropriate fractions, and concentrate under reduced pressure. Triturate with isopropyl ether-petroleum ether and filter to give the title compound AA as a white solid (1.1 g, m.p. 83°-85° C.).

1. customrecool to 10° C
2. temperatureWarm
3. customreaction mixture up to room temperature slowly
4. stirringstir for 16 hours
5. additionPour onto ice/water (100 mL)
6. filtrationDry organic solution with MgSO4, filter
7. customrotoevaporate to give an oil
8. washchromatograph on silica gel, eluting with 30% ethyl acetate-hexane
9. concentrationconcentrate under reduced pressure
10. customTriturate with isopropyl ether-petroleum ether
11. filtrationfilter