反应详情

A round-bottom flask was charged with 6-(benzylthio)-1-(4-chloro-2-methoxyphenyl)isoquinoline (700 mg, 1.786 mmol), acetonitrile (1.68E+04 μl), acetic acid (630 μl), and water (420 μl) to give a thin suspension. The flask was cooling in an ice-bath for 15 min, then 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (704 mg, 3.57 mmol) was added in one portion, leading to an solution. After 20 min, 2,3,4,5,6-pentafluorophenol (493 mg, 2.68 mmol) and triethylamine (1245 μl, 8.93 mmol) were added in sequence. The cooling bath was removed after a few minutes, and the mixture was warmed to room temperature. The mixture was treated with silica gel then concentrated. More silica gel was added, and the mixture was concentrated from DCM. The impregnated silica gel was eluted onto a pre-equilibrated 40-g column with 0 to 50% EtOAc/Heptane to give perfluorophenyl 1-(4-chloro-2-methoxyphenyl)isoquinoline-6-sulfonate (Intermediate NNN; 432 mg, 0.837 mmol, 46.9% yield) as a white foam. NMR and LC/MS indicated the material was about 82% pure. m/z (ESI) 516.0 (M+H)+.

1. customto give a thin suspension
2. temperatureThe flask was cooling in an ice-bath for 15 min
3. customThe cooling bath was removed after a few minutes
4. additionThe mixture was treated with silica gel
5. concentrationthen concentrated
6. additionMore silica gel was added
7. concentrationthe mixture was concentrated from DCM
8. washThe impregnated silica gel was eluted onto a pre-equilibrated 40-g column with 0 to 50% EtOAc/Heptane