反应详情

温度

110 °C

A re-sealable tube is charged with 6-bromo-1-methyl-1H-indole-3-carboxylic acid methyl ester (850 mg, 1.00 equiv, 3.17 mmol), 4-hydroxypiperidine (491 mg, 1.5 equiv, 4.76 mmol), copper(I) iodide (60.379 mg, 0.1 equiv, 0.32 mmole), proline (73 mg, 0.2 equiv, 0.64 mmol) and potassium carbonate (885 mg, 2 equiv, 6.34 mmol) and purged with nitrogen. Anhydrous dimethyl sulfoxide (2 mL) is added. The tube is closed and the mixture is stirred at 110° C. for 22 h. The mixture is allowed to reach room temperature and aqueous saturated NH4Cl is added. The mixture is extracted with EtOAc (2×). The organic layers are combined, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified via chromatography (40 g silica) eluting with a gradient of 20% to 100% ethyl acetate/hexane to provide the title compound (540 mg, 59%) as a white solid. ES/MS m/z 289.0 (M+1)

1. custompurged with nitrogen
2. additionAnhydrous dimethyl sulfoxide (2 mL) is added
3. customThe tube is closed
4. customto reach room temperature
5. additionaqueous saturated NH4Cl is added
6. extractionThe mixture is extracted with EtOAc (2×)
7. washwashed with water
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue is purified via chromatography (40 g silica)
12. washeluting with a gradient of 20% to 100% ethyl acetate/hexane