Water → HCID 90417307, compound

Participants

Reaction Steps

To a solution of 5-(2-azidoacetyl)indolin-2-one (0.20 g, 1.1 mmol) in DMF (5 ml) was added 10% Pd—C (0.20 g), and the mixture was stirred for 3.5 h at room temperature under H2 atmosphere. The mixture was passed through Celite. To the filtrate was added benzoyl chloride (0.12 ml, 1.1 mmol) and iPr2NEt (0.36 ml, 2.2 mmol), and the reaction mixture was stirred for 1 h at 0° C. H2O and EtOAc were added to the mixture, and insoluble solid was removed by filtration. The filtrate was separated and the organic layer was washed with H2O and brine, dried over Na2SO4 and evaporated. The residue was dissolved in sulfuric acid (2.0 ml) and the mixture was heated for 2 h at 90° C. The mixture was cooled to room temperature, and H2O was added. The mixture was extracted with EtOAc, washed with H2O and brine, dried over Na2SO4 and evaporated. Purification by column chromatography (EtOAc/hex) gave 5-(2-phenyloxazol-5-yl)indolin-2-one (0.07 g, 24%).

Provenance & Evidence