反应详情

To a solution of 2-(5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)phenol (0.406 g, 1.006 mmol) in MeOH 5 mL was added potassium acetate (0.126 mL, 2.012 mmol) followed by the dropwise addition of cyanogen bromide, 3.0M solution in DCM (0.402 mL, 1.207 mmol). The resulting mixture was stirred at RT overnight. The reaction mixture was concentrated, washed with sat. NaHCO3, extracted with DCM, dried over Na2SO4 and concentrated. The resulting product was dissolved in 1,2-dichloroethane followed by the addition of 4.0 M HCl in dioxane (15 mL) and stirred at RT for 1.5 h. The reaction mixture was concentrated, diluted with dichloromethane and washed with saturated NaHCO3 solution, brine, dried over Na2SO4, filtered, concentrated. The crude material was purified by chromatography on silica gel using gradient of 0-100% EtOAc/hexanes to give the desired product. MS m/z=429.8 [M+H]+.

1. concentrationThe reaction mixture was concentrated
2. washwashed with sat. NaHCO3
3. extractionextracted with DCM
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. dissolutionThe resulting product was dissolved in 1,2-dichloroethane
7. additionfollowed by the addition of 4.0 M HCl in dioxane (15 mL)
8. stirringstirred at RT for 1.5 h
9. concentrationThe reaction mixture was concentrated
10. additiondiluted with dichloromethane
11. washwashed with saturated NaHCO3 solution, brine
12. dry with materialdried over Na2SO4
13. filtrationfiltered
14. concentrationconcentrated
15. customThe crude material was purified by chromatography on silica gel using gradient of 0-100% EtOAc/hexanes