Water → Methyl 4-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-3-fluorobenzoate

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Water	HCID 962	—
Edukt	Cesium carbonate	HCID 10796	—
Edukt	2-Fluoro-4-(methoxycarbonyl)benzeneboronic acid	HCID 24824345	—
Edukt	3-((5-Bromofuran-2-yl)methylene)-5-chloroindolin-2-one	HCID 66772829	—
Katalysator	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Lösungsmittel	1,4-Dioxane--water (1/1)	HCID 21886435	—
Produkt	Methyl 4-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-3-fluorobenzoate	HCID 66772791	—

Reaktionsbedingungen

Temperatur	110 °C

Reaktionsschritte

To 3-((5-bromofuran-2-yl)methylene)-5-chloroindolin-2-one (150 mg, 0.466 mmol) in dioxane/water (2850/150 μL) was added 2-fluoro-4-(methoxycarbonyl)phenylboronic acid (111 mg, 0.559 mmol) and Cs2CO3 (456 mg, 1.398 mmol). The mixture was degassed with nitrogen for 5 minutes, then PdCl2 dppf (17 mg, 0.023 mmol) was added. The mixture was heated in microwave for 40 minutes at 110° C. Water was added and the solid formed was isolated by filtration to yield methyl 4-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-3-fluorobenzoate. LCMS (M+1=398).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08124649B2
Quelldatensatz	uspto-grants-2012_02
ORD ID	ord-b955915415f340128430572236e447bc
Quellennotiz	uspto-grants-2012_02