Potassium Carbonate → Methyl[6-chloro-2-(4-chloropyridine-2-carbonyl)-1H-indol-3-yl]acetate

Participants

Reaction Steps

A mixture of methyl trans-4-chloro-2-(phenylsulfonylamino)cinnamate (step 1 of Example 8, Method A, 675 mg, 1.92 mmol), 2-bromoacetyl-4-chloropyridine hydrobromide* (907 mg, 2.88 mmol), and potassium carbonate (2.65 g, 19.18 mmol) in acetone (20 ml) was heated at reflux temperature for 4 h. The mixture was cooled and concentrated. The residue was diluted with ethyl acetate (150 ml) and washed with water (70 ml×6). After drying (MgSO4) and removal of solvent, the crude product was purified by flash column chromatography eluting with ethyl acetate/hexane (1:6-1:3) to afford 195 mg (28%) of the title compound (yellow solids) along with 264 mg (27%) of methyl[6-chloro-2-(4-chloropyridine-2-carbonyl)-1-(phenylsulfonyl)indolin-3-yl]acetate (brown crystals).

Provenance & Evidence