1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(5-(3,4-Diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-2-one

Participants

Reaction Steps

To a stirred solution of 3,4-diethoxybenzoic acid (73 mg, 0.35 mmol) in 1,4-dioxane was added EDCI (87 mg, 0.45 mmol) and HOBt (62 mg, 0.45 mmol), the reaction was stirred 20 min at room temperature. To the reaction was added the N-hydroxyimidamide (87 mg, 0.45 mmol) and the mixture was stirred for 30 min at room temperature followed by 16 h at 95° C. The reaction was concentrated under reduced pressure, diluted with EtOAc (80 ml) and washed with brine (2×30 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by column chromatography using CH2Cl2:MeOH (9:1) to offer the product as a pale yellow solid 50% yield (64 mg, 0.175 mmol). MS (EI) m/z: 366 (M+)

Provenance & Evidence