Ethanol → 5-Ethoxy-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

HRID 1633767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633767
[F:1][C:2]1[C:3](/[C:12](/I)=[CH:13]/[C:14](=O)[C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[H-].[Na+].[CH3:24][CH2:25][OH:26]>>[CH2:25]([O:26][C:12]1[CH:13]=[C:14]([C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)[C:5]2[C:6](=[O:11])[NH:7][C:8]3[C:4]=2[C:3]=1[C:2]([F:1])=[CH:10][CH:9]=3)[CH3:24]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 10135347(Z)-5-fluoro-4-[1-iodo-3-oxo-3-(1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one

Produkt 1

HCID 99222075-Ethoxy-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

Versuchsvorschrift

To a suspension of (Z)-5-fluoro-4-[1-iodo-3-oxo-3-(1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one (from Example 8 above) (19.8 mg, 0.05 mmol) in EtOH (5 mL) was added NaH (Aldrich, 60%, 0.1 g, 2.5 mmol) in portions at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was heated under reflux for 2 hours. The reaction was quenched by pouring the reaction mixture into an ice-cold saturated aqueous ammonium chloride solution (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by preparative TLC (silica gel, 50% ethyl acetate in hexanes) to afford 5-ethoxy-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 3.0 mg, 20.1%).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe reaction was quenched
  4. additionby pouring the reaction mixture into an ice-cold saturated aqueous ammonium chloride solution (10 mL)
  5. extractionextracted with ethyl acetate (3×20 mL)
  6. washThe combined organic extracts were successively washed with water (10 mL) and brine (10 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by preparative TLC (silica gel, 50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7311af2ecdeb4ffda655d1965abe2365
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06504034B2

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