Ethyl 3-phenylprop-2-enoate → 3-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

Participants

Reaction Steps

A stirring mixture of 4-bromo-7-methoxyindole LII (162 mg, 0.717 mmol), ethyl cinnamate (254 mg, 1.43 mmol), tetra-butylammonium bromide (46 mg, 0.143 mmol), TEA (199 μl, 1.43 mmol) and palladium-dichloro-[bis-(tri-ortho-tolyl)phosphine] (28 mg, 0.036 mmol) in DMF (2 ml) was heated in a sealed vial flushed with N2, at 110° C. for 20 hours. The reaction was cooled to room temperature and partitioned between H2O and EtOAc. The organic layer was separated and the aqueous layer was extracted twice with EtOAc. The organics were combined dried over Na2SO4, filtered and evaporated. The crude mixture was purified via flash chromatography (hexane/EtOAc) affording 3-(7-methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester LIII (108 mg, 34% yield).

Provenance & Evidence