Benzoic Acid → Oxindole

Participants

Reaction Steps

To a solution of (E)-3-(5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzoic acid (541 mg, 1.48 mmol) and HOBt (400 mg, 2.96 mmol) in DMF (2 mL) was added EDCI (565 mg, 2.96 mmol). The reaction was stirred at rt for 10 min and then added 1-methyl homopiperazine (0.734 mL, 5.92 mmol) followed by DIEA (1 mL). The reaction mixture was stirred at rt for 1 h and diluted with H2O (10 mL). The mixture was extracted with EtOAc, dried over Na2SO4 and concentrated. The crude was purified by preparative TLC eluting with 2% methanol in dichloromethane to give (E)-5-chloro-3-(5-(3-(4-methyl-1,4-diazepane-1-carbonyl)phenyl)furan-2-yl)methylene)indolin-2-one. LCMS (ES): m/z 462 [M+1]+.

Provenance & Evidence