Pyridine → 3-(3-(Pyridin-2-yl)-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

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Reaction Steps

To a stirred suspension of 3-(3-(pyridin-2-yl)-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-3,3a,4,5-tetrahydronaphtho[1,2-c]isoxazol-3-ol (Preparation 63E, 0.081 g, 0.190 mmol) in anhydrous toluene (2.0 mL) at room temperature was added thionyl chloride (0.028 mL, 0.379 mmol) followed by pyridine (3.07 μl, 0.038 mmol). The reaction mixture was stirred at room temperature for 30 min. and then at 80° C. for 15 min. The reaction mixture was cooled to room temperature and concentrated. The solid residue was diluted with dichloromethane (30 mL), washed with a saturated aqueous solution of sodium bicarbonate (10 mL), and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded a tan solid. The crude products were combined and triturated with methanol with sonication. The solid was collected to provide 3-(3-(pyridin-2-yl)-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (0.098 g, 0.239 mmol, 64% yield) as a tan solid. The product had an HPLC with a ret. time=3.36 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=409.9.

Provenance & Evidence