Potassium Carbonate → [6-Chloro-2-(4-methylpyridine-2-Carbonyl)-1H-indol-3-yl]acetic Acid

Participants

Reaction Steps

A mixture of methyl trans-4-chloro-2-(ethoxycarbonylamino)cinnamate (step 1, 1.5 g, 5.3 mmol), 2-bromoacetyl-4-methylpyridine hydrobromide*, potassium carbonate (7.3 g, 53 mmol) and acetonitrile (50 ml) was heated at reflux temperature for 17 h. The mixture was then cooled and concentrated. The residue was diluted in ethyl acetate (200 ml) and washed with water (200 ml) and brine (200 ml). After drying (MgSO4) and removal of solvent, the crude product was purified by flash column chromatography eluting with ethyl acetate/hexane (1:5) to afford 433 mg (20%) of the title compound.

Provenance & Evidence