Water → (3E)-3-[5,5-dimethyl-4-(6-vinylpyridin-3-yl)furan-2(5H)-ylidene]-6-fluoro-1,3-dihydro-2H-indol-2-one

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Reaktionsgleichung

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:14])([CH3:13])[O:11]/[C:10](=[C:15]3/[C:16](=[O:25])[NH:17][C:18]4[C:23]/3=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=4)/[CH:9]=2)=[CH:4][CH:3]=1.[CH:26]([B-](F)(F)F)=[CH2:27].[K+].C(N(CC)CC)C.O>C(O)(C)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][C:12]1([CH3:14])[O:11]/[C:10](=[C:15]2/[C:16](=[O:25])[NH:17][C:18]3[C:23]/2=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)/[CH:9]=[C:8]1[C:5]1[CH:6]=[N:7][C:2]([CH:26]=[CH2:27])=[CH:3][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 76 °C

Versuchsvorschrift

A mixture of 3-[4-(6-chloro-pyridin-3-yl)-5,5-dimethyl-5H-furan-(2E)-ylidene]-6-fluoro-1.3-dihydro-indol-2-one (60 mg, 0.17 mmol), potassium vinyltrifluoroborate (40 mg, 0.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with CH2Cl2, 10 mg, 0.012 mmol) and triethylamine (60 mg, 0.59 mmol) in isopropanol/water (10 mL/5 mL) solution was heated at 76° C. under nitrogen for 2.5 hours. The reaction was cooled to room temperature and poured into 100 mL of water. The resulting precipitates were filtered, washed with water and dried in vacuo to give (3E)-3-[5,5-dimethyl-4-(6-vinylpyridin-3-yl)furan-2(5H)-ylidene]-6-fluoro-1,3-dihydro-2H-indol-2-one as a brown solid. Yield: 50 mg, 85%.

Aufarbeitung

temperatureThe reaction was cooled to room temperature
customThe resulting precipitates
filtrationwere filtered
washwashed with water
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-783cb767cacf4e6492e3e2a2373f063c
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08877923B2

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