Triethylamine → perfluorophenyl 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate

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Reaction Steps

To a solution of 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride (220 mg, 0.603 mmol) in DCM (5 mL) was added pentafluorophenol (110 mg, 0.603 mmol) at 0° C. Triethylamine (0.12 mL, 0.904 mmol) was added at 0° C. and the reaction mixture was stirred at room temperature for 1 h. After completion, the reaction mixture was diluted with DCM (3 mL) and concentrated under reduced pressure. The crude mass thus obtained was purified by column chromatography (12 g column; elution: 5% ethyl acetate in hexane) to get perfluorophenyl 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate (180 mg, 58.4%) as a clear liquid. m/z (ESI) 512.0 (M+H)+.

Provenance & Evidence