Ethyl 3-phenylprop-2-enoate → 3-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-5-methoxyindole XLVI (104 mg, 0.46 mmol), ethyl cinnamate (162 mg, 0.92 mmol), tetra-butylammonium bromide (29.6 mg, 0.092 mmol), TEA (128 μl, 0.092 mmol) and palladium-dichloro-[bis(tri-ortho-tolyl)phosphine] (18 mg, 0.023 mmol) in DMF (2 ml) was stirred at 110° C. for 3 hours. The reaction mixture was cooled to room temperature and partitioned between brine and EtOAc. The organic layers were combined, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 3-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester XLVIII (37 mg, impure).

Provenance & Evidence