Dimethylformamide → 3-(2-ethoxypyridin-3-yl)-6-fluoro-3-hydroxy-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

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Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6](=[O:12])[C:5]2([C:14]1[C:15]([O:20][CH2:21][CH3:22])=[N:16][CH:17]=[CH:18][CH:19]=1)[OH:13].[CH3:23][N:24](C)C=O>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[CH2:21]([O:20][C:15]1[C:14]([C:5]2([OH:13])[C:4]3[C:8](=[CH:9][C:10]([F:11])=[C:2]([C:23]#[N:24])[CH:3]=3)[NH:7][C:6]2=[O:12])=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

161 mg (0.14 mmol) of tetrakis(triphenylphosphine)palladium (0) were added to a solution of 1.7 g (4.63 mmol) of 5-bromo-3-(2-ethoxypyridin-3-yl)-6-fluoro-3-hydroxy-1,3-dihydroindol-2-one from example a.1 and 544 mg (4.63 mmol) of zinc cyanide in 18 ml of dimethylformamide (DMF), and the mixture was agitated in a Biotage microwave apparatus at 150° C. for 1 h. The reaction solution was worked up by diluting with 300 ml of water, extracting with ethyl acetate (3×) and washing with saturated sodium chloride solution (1×). The combined organic phases were dried over magnesium sulfate and filtered, and the solvent was removed in vacuo. 1.67 g of 3-(2-ethoxypyridin-3-yl)-6-fluoro-3-hydroxy-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile were obtained.

Aufarbeitung

extractionextracting with ethyl acetate (3×)
washwashing with saturated sodium chloride solution (1×)
dry with materialThe combined organic phases were dried over magnesium sulfate
filtrationfiltered
customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-3d66e1251699412a938594a2ea4fe583
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08546401B2

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