反应详情

A round-bottom flask was charged with perfluorophenyl 1-chloroisoquinoline-6-sulfonate (see EXAMPLE 73, Step 1; 555 mg, 1.355 mmol), 2-chloro-4-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (INTERMEDIATE UUUU, 477 mg, 1.626 mmol), potassium carbonate (562 mg, 4.06 mmol), and Pd(Ph3P)4 (157 mg, 0.135 mmol). The vial was flushed with Ar (g), then 1,4-dioxane (5080 μl) and water (1693 μl) were added. The flask was lowered into a 50° C. heating bath for 1 h. The reaction mixture was diluted with water and EtOAc. The organic extract was dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 0-50% EtOAc/Heptane) to give perfluorophenyl 1-(4-chloro-5-cyano-2-methoxyphenyl)isoquinoline-6-sulfonate (583.89 mg, 1.080 mmol, 80% yield) as an off-white foam. m/z (ESI) 540.9 (M+H)+.

1. customThe vial was flushed with Ar (g)
2. addition1,4-dioxane (5080 μl) and water (1693 μl) were added
3. customwas lowered into a 50° C.
4. temperatureheating bath for 1 h
5. additionThe reaction mixture was diluted with water and EtOAc
6. extractionThe organic extract
7. dry with materialwas dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 0-50% EtOAc/Heptane)