Triethylamine → HCID 86687467, compound

Participants

Reaction Steps

To a vial charged with 7-(benzylthio)-4-bromoisoquinoline (0.570 g, 1.726 mmol) was added acetonitrile (16.24 ml), acetic acid (0.609 ml), water (0.406 ml). The resulting solution was cooled in an ice water bath and 1,3-dichloro-5,5-dimethyl-2-imidazolidinedione (0.453 ml, 3.45 mmol) was added. After 1 hr LC/MS of the resulting solution indicated product, 4-bromoisoquinoline-7-sulfonyl chloride, as the primary species. m/z (ESI) 306.0 (M+H)+. To the mixture was added 2,3,4,5,6-pentafluorophenol (0.361 ml, 3.45 mmol) and triethylamine (0.962 ml, 6.90 mmol) affording a yellow solution. After 45 min LC/MS indicated conversion to desired product (PFP ester). The mixture was diluted with EtOAc and extracted with H2O. The aqueous phase was extracted with EtOAc. The combined organics were dried with Na2SO4, filtered, and dried under reduced pressure. The crude material was purified with a 40 g silicycle HP column (SiliCycle, Inc. Quebec City, Canada) ramping EtOAc in heptane (0-15%) providing product as a pale yellow oil, perfluorophenyl 4-bromoisoquinoline-7-sulfonate (0.618 g, 1.361 mmol, 79% yield). m/z (ESI) 454.1 (M+H)+.

Provenance & Evidence