Potassium Carbonate → HCID 21071010, compound

HRID 1372130Notes

Reaction equation

HRID 1372130 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]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][N:31]=[CH:30]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:32]3[C:33]4[C:29](=[CH:28][C:27]([N+:24]([O-:26])=[O:25])=[CH:35][CH:34]=4)[CH:30]=[N:31]3)[CH2:6][CH2:7]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 18485111-(Chloroacetyl)-4-(4-fluorophenyl)piperazine

Product 1

HCID 21071010HCID 21071010, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

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 1h under nitrogen. 5-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 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 on purification on neutral alumina column (pet ether/ethyl acetate) gave title compound as a pale yellow solid.

Workup

  1. temperaturecooled
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialDrying of the organic layer with Na2SO4
  5. concentrationfollowed by concentration
  6. customafforded material
  7. customthat on purification on neutral alumina column (pet ether/ethyl acetate)

Sources & evidence

ORD record
ord-077f862e94e545848c573aa37e863089
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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