Reaktion #471004

Reaktionsgleichung

Cesium carbonate

2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

ethyl 7-bromobenzofuran-2-carboxylate

1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone

→

product

Ausbeute 61.5%

Ethyl 7-(4-(2-(1-acetylindolin-5-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate

Ausbeute 61.5%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigein dry
2. 2
   Sonstigedegassed dioxane (8 mL)
3. 3
   TemperaturAfter cooling to room temperature
4. 4
   workup.ADDITIONwater and DCM were added
5. 5
   Sonstigethe layers separated
6. 6
   ExtraktionThe aq phase was extracted with DCM (3×)
7. 7
   WaschenThe combined organic phases were washed with water
8. 8
   Trocknendried (MgSO4)
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated
11. 11
    SonstigeThe crude product was purified by flash chromatography (DCM/MeOH 95/5)

Vorschrift

Cesium carbonate (0.724 g, 2.22 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.081 g, 0.17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.078 g, 0.09 mmol) were added under argon to a mixture of ethyl 7-bromobenzofuran-2-carboxylate (0.460 g, 1.71 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.491 g, 1.79 mmol) (example 38c) in dry degassed dioxane (8 mL) and the reaction was heated at 95° C. over night. After cooling to room temperature, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography (DCM/MeOH 95/5) to give 0.485 g (61%) of the product.

Quelle