1-{2-[(3-Aminophenyl)ethynyl]phenyl}urea → 2-(3-aminophenyl)-1H-indole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

The mixture of 1-{2-[(3-aminophenyl)ethynyl]phenyl}urea (1.25 g, 5 mmol, 1 eq) in anhydrous CH3CN (35 mL) was bubbled with anhydrous nitrogen for about 15 minutes, followed by the addition of bis(acetonitrile)dichloropalladium (II) (259 mg, 0.2 eq). The resulting mixture was heated at 90° C. for 2 hours, then another batch of bis(acetonitrile)dichloropalladium (II) (259 mg, 0.2 eq) was added and the reaction was continued at 90° C. for 3 hours. The reaction mixture was then concentrated under reduced pressure to remove some of the acetonitrile solvent and the residue was taken into ethyl acetate. The organic solvent mixture was washed with water, brine, and dried with anhydrous sodium sulfate. The solvent mixture was filtered, the filtrate was isolated and concentrated, and the resulting solid residue was subject to a gradient column chromatography [from dichloromethane to MeOH-DCM (1:20)] to yield 2-(3-aminophenyl)-1H-indole-1-carboxamide as a yellow solid (184 mg).

Provenance & Evidence