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

HRID 96

Reaktionsgleichung

Reaktionsgleichung von HRID 96
CC(=O)N1CCc2cc(CCN3CCNCC3)ccc21.CCOC(=O)c1cc2cccc(Br)c2o1>C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CCOC(=O)c1cc2cccc(N3CCN(CCc4ccc5c(c4)CCN5C(C)=O)CC3)c2o1

Komponenten

7

Edukt 2

HCID 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 61,47 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10796Cesium carbonateReagenzHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

06/05 2009 14:53:56 +0200 To 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) (from EN02198-74) in dry degassed dioxane (8 mL) were added 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) under argon and the reaction heated at 95°C overnight. After cooling to rt, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (MgSO4), filtered and evaporated. The crude was purified by flash (SiO2; DCM/MeOH 95/5) to give 0.485 g (61%) of the product as a yellow solid.

Quellen und Nachweise

ORD-Eintrag
ord-90e612e9a6744ee3af3c528f17e1b1ce
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
Quelle ansehen

Verknüpfte Notizen

Wird geladen…