Pyridine → HCID 67171508, compound

Participants

Reaction Steps

To a stirred suspension of 7-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazol-3-ol (Preparation 61A, 0.035 g, 0.070 mmol) in anhydrous toluene (1.0 mL) at room temperature was added pyridine (0.012 mL, 0.153 mmol) followed by thionyl chloride (8.64 μl, 0.118 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 diluted with dichloromethane, washed with a saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded a yellow film. The combined crude products were triturated with methanol with sonication. The solid was collected to provide 7-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[4,3-c]isoxazole (0.042 g, 0.087 mmol, 62% yield) as an off-white solid. The product had an HPLC with a ret. time=3.63 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=484.9.

Provenance & Evidence