反应详情

温度

60 °C

Subject a mixture of methyl-5-bromonicotinate (1.0 g, 4.63 mmol), triethylsilane (0.807 g, 6.94 mmol), tetrakis(triphenylphosphino)palladium (0) (0.531 g, 0.460 mmol), and triethylamine (1.03 g, 10.18 mmol) in acetonitrile (10 mL) to an atmosphere of carbon monoxide gas (20 psi) heated at 60° C. for 5 h. Cool the reaction to room temperature and then absorb directly onto silica gel. Purify the residue by chromatography over silica gel, eluting with hexanes/ethyl acetate (80:20), to provide the title compound as an oil (0.114 g, 15%). 1H NMR (CDCl3, 300 MHz) δ 3.90 (s, 3H), 7.35-7.50 (m, 1H), 8.32-8.42 (m, 1H), 8.77-8.90 (m, 1H), 9.23 (s, 1H); TLC Rf=0.37 (4:1 Hexanes/Ethyl Acetate).

1. temperatureCool
2. customthe reaction to room temperature
3. customabsorb directly onto silica gel
4. customPurify the residue by chromatography over silica gel
5. washeluting with hexanes/ethyl acetate (80:20)