HCID 66676088, Verbindung → 5-tert-butyl-6-nitro-1H-indole

HRID 423780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423780
[C:1]([C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([NH:14][C:15]#[C:16][Si](C)(C)C)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.[Cu]I>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:14][CH:15]=[CH:16]2)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 66676088HCID 66676088, Verbindung

Produkt 1

HCID 574702075-tert-butyl-6-nitro-1H-indoleAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a solution of 4-tert-butyl-5-nitro-2-trimethylsilanylethynyl-phenylamine (25 g, 86 mmol) in DMF (100 mL) was added CuI (8.2 g, 43 mmol) under a nitrogen atmosphere. The mixture was heated at 135° C. in a sealed pressure flask overnight, cooled down to room temperature and filtered through a short plug of Celite. The filter cake was washed with EtOAc. The combined filtrate was washed with water, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (10-20% EtOAc/Hexane) to provide 5-tert-butyl-6-nitro-1H-indole as a yellow solid (12.9 g, 69%).

Aufarbeitung

  1. temperaturecooled down to room temperature
  2. filtrationfiltered through a short plug of Celite
  3. washThe filter cake was washed with EtOAc
  4. washThe combined filtrate was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (10-20% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-10957c97d16e40c8973095c11275b8c7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101767B2

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