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

HRID 535650

Reaktionsgleichung

Reaktionsgleichung von HRID 535650
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.Br[C:42]1[C:50]2[O:49][C:48]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[CH:47][C:46]=2[CH:45]=[CH:44][CH:43]=1.[N:56]1([CH2:62][CH2:63][C:64]2[CH:65]=[C:66]3[C:70](=[CH:71][CH:72]=2)[N:69]([C:73](=[O:75])[CH3:74])[CH2:68][CH2:67]3)[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:73]([N:69]1[C:70]2[C:66](=[CH:65][C:64]([CH2:63][CH2:62][N:56]3[CH2:61][CH2:60][N:59]([C:42]4[C:50]5[O:49][C:48]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[CH:47][C:46]=5[CH:45]=[CH:44][CH:43]=4)[CH2:58][CH2:57]3)=[CH:72][CH:71]=2)[CH2:67][CH2:68]1)(=[O:75])[CH3:74]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 46738833Ethyl 7-bromobenzofuran-2-carboxylateHCID 596367471-(5-(2-(Piperazin-1-yl)ethyl)indolin-1-yl)ethanone

Produkt 1

HCID 59636756Ethyl 7-(4-(2-(1-acetylindolin-5-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylateAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customin dry
  2. customdegassed dioxane (8 mL)
  3. temperatureAfter cooling to room temperature
  4. additionwater and DCM were added
  5. customthe layers separated
  6. extractionThe aq phase was extracted with DCM (3×)
  7. washThe combined organic phases were washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash chromatography (DCM/MeOH 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-3830199987214ab39ba092e1b152b6df
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859534B2

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