Potassium Carbonate → 6-(4-Hydroxy-piperidin-1-yl)-1-methyl-1H-indole-3-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

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)

Provenance & Evidence