Water → HCID 86687425, compound

Participants

Reaction Steps

A round-bottom flask was charged with 6-(benzylthio)-1-chloro-4-fluoroisoquinoline (0.088 g, 0.290 mmol), acetonitrile (2.73 ml), acetic acid (0.102 ml), and water (0.068 ml) to give a thin suspension. The flask was cooled in an ice-bath for 10 min, then 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.114 g, 0.579 mmol) was added in one portion, leading to a solution. The reaction was stirred for 30 minutes. 2,3,4,5,6-pentafluorophenol (0.061 ml, 0.579 mmol) was added followed by drop wise addition of triethylamine (0.101 ml, 0.724 mmol). The reaction was stirred for 30 minutes. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (12 g, gradient elution 0 to 25% EtOAc:Heptane) to afford perfluorophenyl 1-chloro-4-fluoroisoquinoline-6-sulfonate as a clear colorless oil. (ESI) 428.1 (M+H)+.

Provenance & Evidence