反应详情

温度

110 °C

A mixture of 5-bromo-2-pyridinecarbaldehyde (1.5 g, 8.064 mmol), 1,1-dimethylethyl methylcarbamate (D83) (1.267 g, 9.677 mmol), tris(dibenzylideneacetone) dipalladium(0) (0.148 g, 0.161 mmol), xantphos (0.373 g, 0.645 mmol) and cesium carbonate (3.678 g, 11.289 mmol) in dioxane (35 mL) was heated at 110° C. overnight under an argon atmosphere. On cooling, the solvent was removed in vacuo and the residue partitioned between EtOAc and water. The organic layer was separated, washed with water and brine, dried and concentrated to give the crude product which was purified by column chromatography. Elution with 0-50% ether/petroleum ether gave the title compound as a brown oil (0.977 g). δH (CDCl3, 400 MHz) 10.01 (1H, s), 8.79 (1H, d), 7.94 (1H, dd), 7.86 (1H, dd), 3.40 (3H, s), 1.53 (9H, s). MS (ES+): 259.1 (MNa+), 181.2, no molecular ion (MH+) observed.

1. temperatureOn cooling
2. customthe solvent was removed in vacuo
3. customthe residue partitioned between EtOAc and water
4. customThe organic layer was separated
5. washwashed with water and brine
6. customdried
7. concentrationconcentrated
8. customto give the crude product which
9. customwas purified by column chromatography
10. washElution with 0-50% ether/petroleum ether