3-Methylbenzoic acid → 2-{3-[(3-methylbenzoyl)amino]phenyl}-1H-indole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To the solution of 2-(3-aminophenyl)-1H-indole-1-carboxamide (50.2 mg, 0.2 mmol, 1 eq) and m-toluic acid (27.5 mg, 1 eq) in anhydrous DCE (2 mL) was added 4-(dimethylamino)pyridine (4.9 mg, 0.2 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (46.1 mg, 1.2 eq). After the reaction was stirred at 60° C. for 1 hour, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper clear solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (EtOAc-Hex 1:10 to 1:1) to give 2-{3-[(3-methylbenzoyl)amino]phenyl}-1H-indole-1-carboxamide as a clear oil which turned into a white foam in vacuo in amount of 34 mg.

Provenance & Evidence