反应详情

Sodium hydride (60% dispersion in oil; 0.20 g, 5.0 mmol) was slowly added to a solution of benzyl 4-{2-[(3-bromopyridin-2-yl)amino]-2-oxoethyl}-3,6-dihydropyridine-1(2H)-carboxylate (1.91 g, 4.43 mmol) in tetrahydrofuran (15 mL) at 0° C. After 30 min, [2-(chloromethoxy)ethyl](trimethyl)silane (0.86 mL, 4.88 mmol) was added. After 4 h, additional sodium hydride (60% dispersion in oil; 0.10 g, 2.5 mmol) was added, followed by [2-(chloromethoxy)ethyl](trimethyl)silane (0.43 mL, 2.44 mmol). After 18 h, the reaction mixture was quenched with saturated ammonium chloride. The mixture was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (60% hexanes/ethyl acetate→30% hexanes/ethyl acetate) gave the title compound (1.51 g). MS 560.1 (M).

1. waitAfter 4 h
2. waitAfter 18 h
3. customthe reaction mixture was quenched with saturated ammonium chloride
4. extractionThe mixture was extracted with dichloromethane
5. dry with materialThe combined organic extracts were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by silica gel chromatography (60% hexanes/ethyl acetate→30% hexanes/ethyl acetate)