Methanol → HCID 67425873, compound

Participants

Reaction Steps

To a solution of phenyl bronic acid (0.47 g; 3.9 mmol), N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (0.5 g; 1.9 mmol) and NEt3 (0.5 μl; 3.9 mmol) in CH2Cl2 (15 ml) is added molsieves (150 mg; 4 Å), Cu(OAc)2 (70 mg; 385 μmol) and finally TEMPO (0.33 g; 2.11 mmol). The reaction mixture is stirred in an open flask at RT for 7 days. After completion MeOH (20 ml) is added and the mixture is adsorbed on silica gel. Purification by chromatography gives N-(3,3-dimethyl-6-nitro-2-oxo-1-phenyl-2,3-dihydro-1H-indol-5-yl)-acetamide (0.35 g). The material is de-acetylated in MeOH (10 ml) using DBU (80 μl) at reflux. After aqueous work-up 5-amino-3,3-dimethyl-6-nitro-1-phenyl-1,3-dihydro-indol-2-one (0.3 g) is obtained and used without further purification.

Provenance & Evidence