Pyridine → HCID 58374162, compound

Participants

Reaction Steps

To a mixture of 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (0.200 g, 0.843 mmol) and pyridine (0.082 mL, 1.01 mmol) in dichloromethane (8 mL) at room temperature was added 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (0.085 mL, 1.01 mmol). The reaction mixture was stirred at room temperature overnight. The heterogeneous reaction was diluted with dichloromethane, washed with an ice-cold solution of 0.5N aqueous hydrochloric acid (2×), and the organic layer was collected. The aqueous layer was back-extracted with dichloromethane, and the combined organic layers were dried anhydrous sodium sulfate and concentrated to afford 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (0.130 g, 0.544 mmol, 65% yield) as a yellow solid. The product had an HPLC ret. time=2.51 min. (corresponding to the methyl ester)−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.

Provenance & Evidence