Water → 3-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-5-methyl-[1,2,4]oxadiazole

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Reaction Steps

To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-hydroxy-2-methyl-benzamidine (i.e product of Step 1, 400 mg, 0.93 mmol) in pyridine (10 mL) was added acetyl chloride (0.13 mL, 0.15 g, 1.85 mmol) via syringe and the mixture was stirred at reflux for 30 min. Water and EtOAc were added after cooling and the aqueous layer was extracted with EtOAc. Combined organic layers were dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography on silica gel and yielded the title compound (277 mg, 65%).

Provenance & Evidence