反应详情

温度

70 °C

A mixture of tert-butyl 6-amino-3-bromo-2-hydroxybenzoate (Intermediate 62, 1.16 g), 2-formylfuran-3-boronic acid pinacol ester (1.073 g), tris-(dibenzylideneacetone)dipalladium (0.184 g), tri-tert-butylphosphonium tetrafluoroborate (0.117 g) and cesium carbonate (3.935 g) was suspended in dioxane (40 mL) and water (5 mL). The mixture was de-gassed and flushed with nitrogen then heated at 70° C. for 3 hours. After cooling, the mixture was concentrated in vacuo. The residue was partitioned between water and ethyl acetate and the combined organic layers were dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 2.5-25% to give tert-butyl 6-amino-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (0.854 g) as a yellow oil.

1. customThe mixture was de-gassed
2. customflushed with nitrogen
3. temperatureAfter cooling
4. concentrationthe mixture was concentrated in vacuo
5. customThe residue was partitioned between water and ethyl acetate
6. dry with materialthe combined organic layers were dried (MgSO4)
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo
9. customthe residue was purified by chromatography on silica
10. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 2.5-25%