Water → HCID 67168993, compound

Participants

Reaction Conditions

Reaction Steps

To a homogeneous solution of tert-butyl 7-bromo-4-morpholinoquinoline-1(2H)-carboxylate (Preparation 77A, 0.598 g, 1.513 mmol) and triethylamine (0.419 mL, 3.03 mmol) in acetonitrile (20 mL) at 0° C. was added a solution of 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (I-4, 0.392 g, 1.51 mmol) in acetonitrile (1.0 mL). The reaction mixture was stirred at 0° C. for 2.5 hours and then overnight at room temperature. A homogeneous solution of hydroxylamine hydrochloride (0.421 g, 6.05 mmol) and sodium acetate (0.496 g, 6.05 mmol) in water (0.981 mL, 54.5 mmol) was added, and the reaction mixture was heated at 45° C. for 60 min. The reaction mixture was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. Concentration under vacuum afforded the crude product which was chromatographed using silica gel chromatography eluting with a 10% mixture of ethyl acetate in hexane to give tert-butyl 7-bromo-3-hydroxy-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-3a,4-dihydroisoxazolo[4,3-c]quinoline-5(3H)-carboxylate (0.050 g, 0.086 mmol, 6% yield) as a yellowish solid. The product had LC/MS M+1=636.2 and 637.2.

Provenance & Evidence