反应详情

A round-bottom flask was charged with 6-(benzylthio)-3-chloroisoquinoline (1.363 g, 4.77 mmol), acetonitrile (44.9 ml), and acetic acid (1.683 ml) to give a suspension. The flask was sonicated for 10 min to give an opaque yellow mixture. Water (1.122 ml) was added, and the mixture became a thin suspension. The flask was cooled in an ice-water bath for 20 min, then 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (1.879 g, 9.54 mmol) was added in one portion, resulting in the formation of a clear solution within 20 sec. After 15 min, 2,3,4,5,6-pentafluorophenol (1.756 g, 9.54 mmol) and triethylamine (2.66 ml, 19.08 mmol) were added in sequence. After another 25 min of stirring, the mixture was diluted with EtOAc (50 mL) and washed with water (2×50 ml), washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was dissolved in DCM and purified by chromatography on silica gel (40-g column, 25-g silica gel loading column, 0 to 30% EtOAc/Heptane) to give perfluorophenyl 3-chloroisoquinoline-6-sulfonate (1.69522 g, 4.14 mmol, 87% yield) as a clear oil contaminated with some pentafluorophenol: m/z (ESI) 286.2 (M+H)+.

1. customto give a suspension
2. customThe flask was sonicated for 10 min
3. customto give an opaque yellow mixture
4. temperatureThe flask was cooled in an ice-water bath for 20 min
5. customresulting in the formation of a clear solution within 20 sec
6. washwashed with water (2×50 ml)
7. washwashed with brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. dissolutionThe residue was dissolved in DCM
12. custompurified by chromatography on silica gel (40-g column, 25-g silica gel loading column, 0 to 30% EtOAc/Heptane)