反应详情

温度

-78 °C

To a mixture of anhydrous CuCN (2.7 g, 30.4 mmol) in 100 mL of THF was added a solution of tert-butylmagnesium chloride (30.4 mL, 60.2 mmol, 2M solution in THF) under N2 at −78° C. After 20 minutes, tert-butyl 5-bromopyridin-2-ylcarbamate (2.1 g, 7.6 mmol, Aldrich) was added. The reaction mixture was stirred for 2 hours at −78° C. and then at room temperature for 12 hours. The mixture was quenched with saturated aqueous NH4OH and basified to pH 7 with 20% aqueous NaOH. The solid was filtered through a pad of Celite. The filtrate was extracted with ether and washed with water. The organic extract was dried over MgSO4 and concentrated. Purification by column chromatography (SiO2,: 0-15% hexanes/ethyl acetate gradient) afforded 0.4 g of the title compound. MS (ESI+) m/z 251 (M+H)+.

1. waitat room temperature for 12 hours
2. customThe mixture was quenched with saturated aqueous NH4OH and basified to pH 7 with 20% aqueous NaOH
3. filtrationThe solid was filtered through a pad of Celite
4. extractionThe filtrate was extracted with ether
5. washwashed with water
6. extractionThe organic extract
7. dry with materialwas dried over MgSO4
8. concentrationconcentrated
9. customPurification by column chromatography (SiO2,: 0-15% hexanes/ethyl acetate gradient)