Reaktion #360703

Reaktionsgleichung

7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine

1-[2-(3-bromo-phenoxy)-ethyl]-pyrrolidine

cesium carbonate

4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene

→

desired product

Ausbeute 154.3%

3-(2-pyrrolidin-1-yl-ethoxy)-phenyl-amine

Ausbeute 154.3%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reactants were flushed with argon
2. 2
   workup.ADDITIONdiluted with dioxane (8 mL)
3. 3
   Temperaturwith reflux condenser
4. 4
   TemperaturThe reaction was heated
5. 5
   Temperaturto reflux for 18 hours
6. 6
   Filtrationfiltered hot
7. 7
   workup.ADDITIONthe solvents were diluted with ethyl acetate
8. 8
   Waschenwashed with brine
9. 9
   ExtraktionThe brine layer was back extracted once with fresh ethyl acetate
10. 10
    Trocknendried over sodium sulfate (Na2SO4)
11. 11
    FiltrationFiltration
12. 12
    Sonstigefollowed by evaporation and column chromatography (1:5 MeOH/DCM)

Vorschrift

In a dry 25 mL round bottom flask, 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (0.113 g, 0.377 mmol, 1 equiv), 1-[2-(3-bromo-phenoxy)-ethyl]-pyrrolidine (0.153 g, 0.565 mmol, 1.5 equiv), cesium carbonate (0.368 g, 1.13 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.044 g, 0.0753 mmol, 0.2 equiv) and tris(dibenzylideneacetone)dipalladium (0.034 g, 0.0376 mmol, 0.1 equiv) were combined. The reactants were flushed with argon, diluted with dioxane (8 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 and column chromatography (1:5 MeOH/DCM) provided desired product as a yellow powder (0.12 g, 65% yield). MS (ESI+): m/z=491.1, LC retention time: 2.94 min.

Quelle