Pyridine → HCID 58374162, compound

Participants

Reaction Steps

To a mixture of 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (0.070 g, 0.295 mmol) and pyridine (0.029 mL, 0.354 mmol) in dichloromethane (2.5 mL) at room temperature was added 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (0.030 mL, 0.354 mmol). The reaction mixture was stirred at room temperature for 5.5 h. The heterogeneous reaction was complete by HPLC and 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 with anhydrous sodium sulfate and concentrated to afford 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (0.050 g, 0.209 mmol, 70.8% yield) as a yellow solid. The product had an HPLC ret. time=2.52 min (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