Cesium carbonate → N-(3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)methanesulfonamide

온도

95 °C

7-bromo-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (5.00 g. 15.7 mmol), methyl sulfonamide (1.49 g, 15.7 mmol), Pd2(dba)3 (0.714 g, 0.78 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino) xanthene (XANTPHOS) (1.36 g, 2.35 mmol) and cesium carbonate (15.3 g, 47.0 mmol) were added to a dry flask through which argon was purged. The flask was charged with 100 mL of dry dioxane and argon was bubbled through the solution for 10 minutes. The reaction mixture was heated to 95° C. and stirred under argon. After 12 hours, the reaction mixture was concentrated and dissolved in 2000 mL ethyl acetate and 1000 mL water. The organic layer was separated and washed with 500 mL of brine, dried with magnesium sulfate, filtered, and concentrated. The resultant solids were dissolved in 150 mL of a 3:1 mixture of hot dichloromethane/methanol and allowed to cool to ambient temperature with stirring. After 3 h, 150 mL of hexanes were added and the resulting slurry was allowed to stir. After 12 hours, an additional 50 mL hexanes were added. After 4 hours, the solids were filtered and dried to afford the title compound.

1. customwas purged
2. additionThe flask was charged with 100 mL of dry dioxane and argon
3. customwas bubbled through the solution for 10 minutes
4. concentrationthe reaction mixture was concentrated
5. dissolutiondissolved in 2000 mL ethyl acetate
6. customThe organic layer was separated
7. washwashed with 500 mL of brine
8. dry with materialdried with magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. dissolutionThe resultant solids were dissolved in 150 mL of a 3:1 mixture of hot dichloromethane/methanol
12. temperatureto cool to ambient temperature
13. stirringwith stirring
14. waitAfter 3 h
15. addition150 mL of hexanes were added
16. stirringto stir
17. waitAfter 12 hours
18. additionan additional 50 mL hexanes were added
19. waitAfter 4 hours
20. filtrationthe solids were filtered
21. customdried

ORD 기록

ord-431626060b9346e5a7d12e1bf601d77a

출처 데이터셋

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08207186B2