7-Nitroindazole → 1-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2-[7-nitro-indazol-1-yl]-ethanone

HRID 270915

Reaktionsgleichung

Reaktionsgleichung von HRID 270915
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[N+:24]([C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:35]=1[NH:34][N:33]=[CH:32]2)([O-:26])=[O:25]>CN(C=O)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:34]3[C:35]4[C:31](=[CH:30][CH:29]=[CH:28][C:27]=4[N+:24]([O-:26])=[O:25])[CH:32]=[N:33]3)[CH2:6][CH2:7]2)=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 18937-NitroindazoleHCID 11430Potassium CarbonateHCID 18485111-(Chloroacetyl)-4-(4-fluorophenyl)piperazine

Produkt 1

HCID 210710111-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2-[7-nitro-indazol-1-yl]-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

2-Chloro-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone (0.834 g, 3.3 mmol) was taken in dry DMF (15 mL) and dry potassium carbonate (1.6 g, 11.6 mmol) was added to it and the reaction mixture stirred at room temperature for 1 h under nitrogen. 7-Nitro-1H-indazole (0.5 g, 2.9 mmol) in DMF (2 mL) was then added to the mixture through a syringe. The reaction was then heated at 70° C. for 14 h, cooled and then quenched with water and extracted with ethyl acetate. Drying of the organic layer with Na2SO4 followed by concentration afforded material that was purified on neutral alumina column (pet ether/ethyl acetate). The resulting solid was recrystallized from DCM/pet ether to obtain pure product as a pale yellow solid.

Aufarbeitung

  1. temperatureThe reaction was then heated at 70° C. for 14 h
  2. temperaturecooled
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialDrying of the organic layer with Na2SO4
  6. concentrationfollowed by concentration
  7. customafforded material that
  8. customwas purified on neutral alumina column (pet ether/ethyl acetate)
  9. customThe resulting solid was recrystallized from DCM/pet ether
  10. customto obtain pure product as a pale yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-91b5f38303c343dbbc8e68d65877a81a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449576B1

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