Water → HCID 58437363, Verbindung

HRID 1674596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1674596
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[NH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:20]([O:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][C:25]=1[O:31][CH2:32][O:33][CH3:34])[CH3:21].O>CN(C)C=O>[CH2:20]([O:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27]([N:5]2[C:6]3[C:11](=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=3)[C:3]([C:1]#[N:2])=[CH:4]2)=[CH:26][C:25]=1[O:31][CH2:32][O:33][CH3:34])[CH3:21]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 584374205,6-difluoro-1H-indole-3-carbonitrileHCID 59224848HCID 59224848, Verbindung

Produkt 1

HCID 58437363HCID 58437363, VerbindungAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 3-cyano-5,6-difluoroindole (0.25 g) in N,N-dimethylformamide (10 mL) were added cesium carbonate (0.91 g), 4-fluoro-2-methoxymethoxybenzoic acid ethyl ester (0.32 g), and this mixture was stirred at 75° C. overnight. This reaction mixture was poured into water, and this resulting mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-75/25) to give the title compound (0.12 g).

Aufarbeitung

  1. extractionthis resulting mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-75/25)

Quellen und Nachweise

ORD-Eintrag
ord-47fe36752ef44b8d9c0038ef7d25f29a
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003647B2

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