反应详情

温度

100 °C

A mixture of methyl 6-Chloro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-1H-indole-3-carboxylate (50 mg, 0.16 mmol), 1-(4-Bromo-3-methoxy-phenyl)cyclobutanol (52 mg, 0.2 mmol), 2 M aqueous potassium carbonate (0.31 mL, 0.63 mmol), toluene (3 mL), and ethanol (1 mL) was sparged with nitrogen for 10 minutes, then treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (6 mg, 0.007 mmol). The reaction mixture was heated to 100° C. and stirred. After 2 hours the reaction was cooled to room temperature, diluted with ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford a yellow oil, which was purified by flash chromatography (12 g silica, 0-35% ethyl acetate/heptane, 24 column volumes). Product fractions were combined and concentrated in vacuo to afford the title compound as a colorless solid (19 mg, 32% yield). MS (ES−) 341.2 (M−H)−; 1H NMR (500 MHz, CD3OD) δ 8.03 (d, J=1.95 Hz, 2 H), 7.60 (s, 1 H), 7.38 (d, J=7.56 Hz, 1 H), 7.06 (d, J=1.46 Hz, 1 H), 7.01 (dd, J=7.68, 1.59 Hz, 1 H), 3.89 (d, J=7.32 Hz, 6 H), 2.65-2.75 (m, 2 H), 2.34-2.44 (m, 2 H), 2.08-2.19 (m, 1 H), 1.70-1.80 (m, 1 H).

1. customwas sparged with nitrogen for 10 minutes
2. temperatureAfter 2 hours the reaction was cooled to room temperature
3. washwashed with water and saturated brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto afford a yellow oil, which
8. customwas purified by flash chromatography (12 g silica, 0-35% ethyl acetate/heptane, 24 column volumes)
9. concentrationconcentrated in vacuo