反应详情

A flask was charged with ethyl 2-(2-chloropyridin-4-yl)acetate (20.00 g, 100.2 mmol), tert-butyl carbamate (35.21 g, 300.5 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (2.90 g, 5.01 mmol), tris(dibenzylideneacetone)dipalladium(0) (2.29 g, 2.51 mmol), cesium carbonate (48.96 g, 150 mmol) and THF (400 mL). The mixture was heated at reflux under nitrogen for 24 hours. Upon cooling, the reaction was quenched with 10% ammonium acetate solution and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried and concentrated. The residue was purified by silica gel chromatography, eluting with 20% ethyl acetate/hexane to yield 20.80 g (72.6% yield) of the desired product as white solid.

1. temperatureThe mixture was heated
2. temperatureat reflux under nitrogen for 24 hours
3. temperatureUpon cooling
4. customthe reaction was quenched with 10% ammonium acetate solution
5. extractionextracted with ethyl acetate
6. washThe combined organic extracts were washed with water and brine
7. customdried
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography
10. washeluting with 20% ethyl acetate/hexane