反应详情

温度

95 °C

To a stirring solution of 4-bromo-2-((tert-butyldimethylsilyloxy)methyl)pyridine INT-70 (0.800 g, 2.6 mmol) in 3 mL of 1-methy-2-pyrrolidine (NMP) was added zinc cyanide (0.610 g, 5.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.060 g, 0.052 mmol). The solution was degassed with N2 and the reaction mixture heated at 95° C. for 12 h. Upon cooling, the reaction mixture was diluted with saturated NaHCO3 and extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by chromatography (MeOH/DCM) to produce 0.170 g (26%) of 2-((tert-butyldimethylsilyloxy)methyl)isonicotinonitrile INT-71 as a light yellow solid. LCMS-ESI (m/z) calculated for C13H20N2OSi: 248.4; found 249.1 [M+H]+, tR=4.21 min (Method 1).

1. customThe solution was degassed with N2
2. temperatureUpon cooling
3. additionthe reaction mixture was diluted with saturated NaHCO3
4. extractionextracted with DCM
5. dry with materialThe combined organic layers were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by chromatography (MeOH/DCM)