反应详情

温度

0 °C

A first flask was charged with 1,4-dioxane/H2O (50 mL/10 mL). The flask was cooled to 0° C. and vacuum was applied for 20 minutes. A second flask was charged with 1-((5-(benzyloxy)-6-methylpyridin-2-yl)methyl)-3-bromo-4-nitro-1H-indazole (6.07 g, 13.4 mmol), cyclopropylboronic acid (4.60 g, 53.6 mmol), diacetoxypalladium (0.150 g, 0.670 mmol), K2CO3 (5.55 g, 40.2 mmol) and sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate (0.686 g, 1.34 mmol). The second flask was also evacuated with vacuum and back filled with N2 for 3 times. The cold degassed dioxane/H2O was added to the second flask, which was evacuated with vacuum and back filled with argon for 5 times. The reaction mix was then heated to 80° C. for 3 hours. A sample (1H NMR) taken from the flask showed complete reaction at this point. The reaction was cooled to ambient temperature, filtered and concentrated under reduced pressure. The residue was diluted with EtOAc (200 mL). The organic layer was washed with saturated NaHCO3, dried (Na2SO4) and concentrated to give desired product, which was used in the next step without further purification.

1. customThe second flask was also evacuated with vacuum
2. additionback filled with N2 for 3 times
3. customThe cold degassed dioxane/H2O
4. additionwas added to the second flask, which
5. customwas evacuated with vacuum
6. additionback filled with argon for 5 times
7. additionThe reaction mix
8. temperaturewas then heated to 80° C. for 3 hours
9. customreaction at this point
10. temperatureThe reaction was cooled to ambient temperature
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. additionThe residue was diluted with EtOAc (200 mL)
14. washThe organic layer was washed with saturated NaHCO3
15. dry with materialdried (Na2SO4)
16. concentrationconcentrated