反应详情

温度

90 °C

A mixture of methyl 5-bromo-6-chloro-1H-indole-3-carboxylate (5.2 g, 18.0 mmol), 2-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenoxy)ethanol (5.7 g, 22.8 mmol), PdCl2(dppf) (0.54 g, 0.72 mmol), 2M aqueous solution of potassium carbonate (27 ml, 54.0 mmol), ethanol (30 ml), and toluene (90 ml) was stirred in a closed bottle at 80° C. for 2 hours and at 90° C. for 2 more hours. The reaction mixture was cooled to room temperature, ethyl acetate (50 ml) was added, and the mixture was filtered through a pad of Celite. The organic phase of the mother liquor was separated. Filter cake was washed with 10% of methanol in THF and this wash was combined with the first organic extract. The combined organic solution was dried over anhydrous magnesium sulfate and loaded on silica gel. Chromatography on a silica gel column, eluting with a gradient from 40% to 90% of ethyl acetate in heptanes to give the title compound (6.15 g, 98%).

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationthe mixture was filtered through a pad of Celite
3. customThe organic phase of the mother liquor was separated
4. filtrationFilter cake
5. washwas washed with 10% of methanol in THF
6. dry with materialThe combined organic solution was dried over anhydrous magnesium sulfate
7. washChromatography on a silica gel column, eluting with a gradient from 40% to 90% of ethyl acetate in heptanes