Benzyl Bromide → 1-Benzyl-5-nitro-1H-indazole

HRID 1292965

Reaktionsgleichung

Reaktionsgleichung von HRID 1292965
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:19]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[N:8]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 215015-Nitroindazole

Produkt 1

HCID 219520821-Benzyl-5-nitro-1H-indazoleAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 5-nitroindazole (10.0 g, 61.3 mmol) in acetonitrile (100 mL) was added potassium carbonate (16.9 g, 122.6 mmol) and benzyl bromide (13.6 g, 79.7 mmol). The resulting yellow reaction mixture was heated with stirring at 70° C. overnight. Upon cooling down, the solid was filtered off and washed with methylene chloride. The filtrate was concentrated to dryness and the resulting residue was purified by flash chromatography eluting with 17–25% ethyl acetate in hexanes (v/v) yielding 7.0 g (44%) of the corresponding 1-Benzyl-5-nitro-1H-indazole as a yellow solid.

Aufarbeitung

  1. temperatureThe resulting yellow reaction mixture was heated
  2. temperatureUpon cooling down
  3. filtrationthe solid was filtered off
  4. washwashed with methylene chloride
  5. concentrationThe filtrate was concentrated to dryness
  6. customthe resulting residue was purified by flash chromatography
  7. washeluting with 17–25% ethyl acetate in hexanes (v/v)

Quellen und Nachweise

ORD-Eintrag
ord-1a4d388626f84811aaef5791b5b36270
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238701B2

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