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

Temperature

90 °C

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).

1. customwas bubbled with anhydrous nitrogen for about 15 minutes
2. concentrationThe reaction mixture was then concentrated under reduced pressure
3. customto remove some of the acetonitrile solvent
4. washThe organic solvent mixture was washed with water, brine
5. dry with materialdried with anhydrous sodium sulfate
6. filtrationThe solvent mixture was filtered
7. customthe filtrate was isolated
8. concentrationconcentrated

ORD record

ord-3b71acd313a94fdebfa617f90d2a6067

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353093B2