Реакция #622814

Уравнение реакции

cesium carbonate

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

Ethyl 7-bromobenzofuran-2-carboxylate

1-(2-(pyridin-2-yl)ethyl)piperazine

→

title compound

Выход 40.0%

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

Выход 40.0%

Растворители

DCM

Water

Условия реакции

Обработка

1. 1
   Другоеin dry
2. 2
   Другоеdegassed dioxane (13 mL)
3. 3
   Другоеthe layers were separated
4. 4
   ЭкстракцияThe aq phase was extracted with DCM (3×)
5. 5
   ПромывкаThe combined organic phases were washed with water
6. 6
   Сушкаdried (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated
9. 9
   ДругоеThe crude product was purified by flash chromatography

Методика

Ethyl 7-bromobenzofuran-2-carboxylate (0.900 g, 3.34 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (0.672 g, 3.51 mmol) were mixed in dry degassed dioxane (13 mL). To this mixture cesium carbonate (1.417 g, 4.35 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.159 g, 0.33 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.153 g, 0.17 mmol) were added under argon and the reaction was heated at 95° C. over night. Water and DCM were added and the layers were 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. (SiO2; DCM/MeOH 95/5) to give 0.507 g (40%) of the title compound.

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