反应详情

In a dry 25 mL round bottom flask, 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (0.157 g, 0.523 mmol, 1 equiv), 4-bromo-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (0.261 g, 0.785 mmol, 1.5 equiv), cesium carbonate (0.512 g, 1.57 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.061 g, 0.10 mmol, 0.2 equiv) and tris(dibenzylideneacetone)dipalladium (0.048 g, 0.052 mmol, 0.1 equiv) were combined. The reactants were flushed with argon, diluted with dioxane (5 mL) and outfitted with reflux condenser. The reaction was heated to reflux for 18 hours, then filtered hot, and the solvents were diluted with ethyl acetate and washed with brine. The brine layer was back extracted once with fresh ethyl acetate. The organic phases were combined and dried over sodium sulfate (Na2SO4). Filtration followed by evaporation provided slightly impure product. Solids were diluted in minimum amount of DCM and precipitated out using excess hexanes. The resulting solids were filtered off and dried to yield a yellow powder (0.276 g, 95% yield). MS (ESI+): m/z=553.3, LC retention time: 2.77 min.

1. customThe reactants were flushed with argon
2. additiondiluted with dioxane (5 mL)
3. temperaturewith reflux condenser
4. temperatureThe reaction was heated
5. temperatureto reflux for 18 hours
6. filtrationfiltered hot
7. additionthe solvents were diluted with ethyl acetate
8. washwashed with brine
9. extractionThe brine layer was back extracted once with fresh ethyl acetate
10. dry with materialdried over sodium sulfate (Na2SO4)
11. filtrationFiltration
12. customfollowed by evaporation
13. customprovided slightly impure product
14. customprecipitated out
15. filtrationThe resulting solids were filtered off
16. customdried