反应详情

To a solution of 3-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-6-carbonitrile (1.0 g, 13.7 mmol) in N,N-dimethylformamide (10 ml) was added sodium hydride (213 mg, 5.33 mmol) under ice-cooling, and the mixture was stirred for 15 min. After stirring, benzyl 2-bromoethyl ether (0.77 ml, 4.88 mmol) was added and the mixture was stirred at 50° C. for 1 hr. The mixture was allowed to cool to room temperature and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give 1-(2-benzyloxyethyl)-3-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-6-carbonitrile (1.44 g, yield 90%).

1. temperaturecooling
2. stirringAfter stirring
3. stirringthe mixture was stirred at 50° C. for 1 hr
4. extractionThe mixture was extracted with ethyl acetate
5. washThe organic layer was washed successively with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationAfter filtration
8. customthe solvent was evaporated under reduced pressure
9. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)