Triethylamine → HCID 86596775, compound

Participants

Reaction Steps

To a solution of 6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methylbenzo[d] isoxazole-5-carboxylic acid (10a) (75.2 mg, 0.188 mmol) in DMF (1.5 mL) was added HOBt (38.2 mg, 0.249 mmol), Et3N (0.080 mL, 0.571 mmol), O-(2-vinyloxyethyl)hydroxylamine (28.5 mg, 0.276 mmol), and EDCI (47.2 mg, 0.246 mmol) at room temperature. After 6 days, the reaction mixture was diluted with EtOAc, washed with saturated aqueous NH4Cl, brine, saturated aqueous NaHCO3, and brine. The organic layer was dried over MgSO4, filtered, concentrated in vacuo, and purified by flash column chromatography using the Biotage system (3% MeOH in CH2Cl2) to give 57.8 mg (63%) of the desired product (11a).

Provenance & Evidence