Pyridine → HCID 67171662, compound

Participants

Reaction Steps

To a stirred suspension of methyl 8-fluoro-3-hydroxy-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-3,3a,4,5-tetrahydronaphtho[1,2-c]isoxazole-7-carboxylate (Preparation 67B, 0.055 g, 0.115 mmol) in anhydrous toluene (1.0 mL) at room temperature was added pyridine (0.2 mL) followed by thionyl chloride (0.014 mL, 0.196 mmol). The reaction mixture was stirred at room temperature for 15 min. and then at 80° C. for 15 min. The reaction mixture was cooled to room temperature and concentrated. The solid residue was partitioned between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The dichloromethane extract was collected and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded methyl 8-fluoro-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carboxylate [0.050 g, 0.109 mmol, 94%] as an off white solid product. The product had an HPLC ret. time=3.28 min. (condition B). LC/MS M+1=459.1.

Provenance & Evidence