Water → 1-Benzyl-5-nitro-1H-indazole

HRID 983424

Reaktionsgleichung

Reaktionsgleichung von HRID 983424
[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+].[C:19]1([CH2:25]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:25]([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:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:25]([N:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 215015-Nitroindazole

Produkt 2

HCID 219520821-Benzyl-5-nitro-1H-indazoleHCID 22560083HCID 22560083, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-nitroindazole (10 g, 61.3 mmol) in DMF (100 mL) was added K2CO3 (12.7 g, 91.9 mmol) and PhCH2Br (7.29 mL, 61.3 mmol). The resulting mixture was stirred at RT for 3.5 days, then poured into 400 mL of H2O. The resulting slurry was filtered, rinsed once with water and dried in vacuo giving a beige solid. A portion of this crude material (2.5 g) was purified by chromatography (SiO2, elution with 1:2 EtOAc-hexanes) giving 1-benzyl-5-nitro-1H-indazole and 2-benzyl-5-nitro-1H-indazole.

Aufarbeitung

  1. filtrationThe resulting slurry was filtered
  2. washrinsed once with water
  3. customdried in vacuo
  4. customgiving a beige solid
  5. customA portion of this crude material (2.5 g) was purified by chromatography (SiO2, elution with 1:2 EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a143097e57ae4084916693887d2a7f21
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06864255B2

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