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

HRID 535632

Reaktionsgleichung

Reaktionsgleichung von HRID 535632
Br[C:2]1[C:10]2[O:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)Cl.O>[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:2]2[C:10]3[O:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:26][CH2:25]1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 566605Piperazine, 2-pyridylethyl-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 46738833Ethyl 7-bromobenzofuran-2-carboxylate

Produkt 1

HCID 59636751Ethyl 7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customin dry
  2. customdegassed dioxane (13 mL)
  3. customthe layers were separated
  4. extractionThe aq phase was extracted with DCM (3×)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-72322f6497fd422bbf594d3e8939f693
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859534B2

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