Pyridine → HCID 58537232, compound

Participants

Reaction Steps

To a solution of 4-(methoxycarbonyl)-3-phenylisoxazole-5-carboxylic acid (100 mg, 0.405 mmol) and pyridine (0.039 mL, 0.485 mmol) in DCM (4 mL) at rt was added cyanuric fluoride (0.041 mL, 0.485 mmol) and the reaction mixture was stirred at rt for 2 hr. The reaction mixture was diluted with dichloromethane (20 ml) and washed with ice-cold 0.5N HCl (20 mL). The aqueous layer was extracted with DCM (10 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated to afford methyl 5-(fluorocarbonyl)-3-phenylisoxazole-4-carboxylate (100 mg, 0.401 mmol, 99% yield) as a colorless oil. The compound was found to react readily with methanol and was characterized as the methyl ester. HPLC retention time=1.59 minutes (PHENOMENEX® Luna 4.6×30 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.1% TFA over a 2 minute gradient. MS: (M+H)=262.15 (methyl ester).

Provenance & Evidence