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

HRID 1372131

Reaction equation

HRID 1372131 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1cd1bd052fb6497594fc50203ce25e3b
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Linked notes

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