反应详情

温度

135 °C

To a solution of (S)-3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (600 mg) in diethyl malonate (11 mL) were added sodium hydride (124 mg), tris(dibenzylideneacetone)dipalladium(0) (81.4 mg) and 2-(di-tert-butylphosphino)biphenyl (26.5 mg) at room temperature. The reaction mixture was stirred at 135° C. for 1½ h. A saturated aq. solution of ammonium chloride and ethyl acetate were added, the phases were separated and the inorganic one was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (10% to 70% ethyl acetate in n-heptane) to yield the title compound as a light yellow oil (514 mg, 71%), MS (ESI+): m/z=474.3 ([M+H]+).

1. customthe phases were separated
2. extractionthe inorganic one was extracted with ethyl acetate (2×)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by flash chromatography on silica gel (10% to 70% ethyl acetate in n-heptane)