反应详情

温度

80 °C

To a solution of 2.03 g (11 mmol) of methyl 2-chloro-6-methylisonicotinate (Aldrich) in 20 mL of DMF (degassed) was added 1.14 g (9.73 mmol) of Zn(CN)2 and 1.18 g (1.02 mmol) of Pd(PPh3)4. The mixture was stirred at 80° C. for 12.5 h, and EtOAc and 20 mL of 10% NH4OH aqueous solution were added. The organic layer was washed with 20 mL of 10% NH4OH and 20 mL of brine. The combined aqueous layers were reextracted with EtOAc and washed with brine. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 1.3 g of methyl 2-cyano-6-methylisonicotinate in 68% yield.

1. washThe organic layer was washed with 20 mL of 10% NH4OH and 20 mL of brine
2. washwashed with brine
3. dry with materialThe combined extracts were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customPurification by flash silica gel chromatography (30% EtOAc/hexanes)