proline dl-form → HCID 59369340, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepane hydrochloride (298 mg, 0.713 mmol), 6-bromo-1-methyl-1H-indole-3-carboxylic acid methyl ester (195 mg, 0.727 mmol), copper (I) iodide (40 mg, 0.208 mmol), DL-proline (60 mg, 0.516 mmol), and potassium carbonate (385 mg, 2.79 mmol) in dimethyl sulfoxide (3 mL) is heated to 100° C. for 18 h under nitrogen atmosphere. Saturated aqueous ammonium chloride is added and the mixture is extracted with ethyl acetate (3×). The combined ethyl acetate layers are washed with water (2×), brine (3×), dried (MgSO4), and concentrated under reduced pressure. The residue is purified via flash chromatography (40 g silica) using a gradient of ethyl acetate in heptane (0 to 70%) to provided the title compound (47 mg, 12%). LC-ES/MS m/z 569.0 (M+1).

Provenance & Evidence