反应详情

温度

50 °C

3-(Benzyloxy)-5-bromopyridine (5.38 g, 20.4 mmol, Harrowven et al. Tetrahedron, 2001, 57, 4447-4454) in DMF (33 mL) was stirred with copper cyanide (2.9 g, 32.6 mmol) at 160° C. for 7 hours. Saturated aqueous sodium hydrogen carbonate solution and ethyl acetate was added and the formed suspension was stirred at 50° C. for 15 minutes. After filtration the liquid phases were separated. The precipitate was triturated with 10% DMF in ethyl acetate (500 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL) at 50° C. and filtration and phase separation were performed. The treatment of the precipitate with saturated aqueous sodium hydrogen carbonate solution and 10% DMF in ethyl acetate was repeated two times and the combined organic phases washed with brine and dried over sodium sulfate. The solution was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (ethyl acetate in hexane, 0 to 65%) to yield 3.13 g 5-(benzyloxy)pyridine-3-carbonitrile.

1. filtrationAfter filtration the liquid phases
2. customwere separated
3. customThe precipitate was triturated with 10% DMF in ethyl acetate (500 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL) at 50° C.
4. filtrationfiltration and phase separation
5. washthe combined organic phases washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationThe solution was concentrated under reduced pressure
8. customthe residue was purified by chromatography on silica gel (ethyl acetate in hexane, 0 to 65%)