Water → 5-Fluoro-1-(2-oxiranylmethyl)-1H-indole

HRID 1532616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532616
[CH2:1]([CH:3]1[O:5][CH2:4]1)Br.[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.[H-].[Na+].O>CN(C=O)C>[CH2:1]([N:12]1[C:13]2[C:9](=[CH:8][C:7]([F:6])=[CH:15][CH:14]=2)[CH:10]=[CH:11]1)[CH:3]1[O:5][CH2:4]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 678615-Fluoroindole

Produkt 1

HCID 155242005-Fluoro-1-(2-oxiranylmethyl)-1H-indoleAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Epibromohydrin (1.4 ml, 16.5 mmole) was added to a stirred solution of 5-fluoroindole (2.0 g, 15 mmole) and sodium hydride (0.66 g, 16.5 mmole) in anhydrous DMF (20 ml), and the mixture was heated at 60° C. under nitrogen for 15 hours. Water (100 ml) was added and the product extracted into CH2Cl2 (3×35 ml). The combined organics were washed with water (25 ml), brine (25 ml) and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave the crude product as a viscous yellow colored oil (2.7 g). This was purified by flash silica gel chromatography (30% ethyl acetate in hexane) to afford the titled product as a viscous oil (2.5 g, 89% yield).

Aufarbeitung

  1. extractionthe product extracted into CH2Cl2 (3×35 ml)
  2. washThe combined organics were washed with water (25 ml), brine (25 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration in vacuo
  5. customgave the crude product as a viscous yellow colored oil (2.7 g)
  6. customThis was purified by flash silica gel chromatography (30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3b2fc20ab0e0475988855526f8b22525
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204274B1

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