Potassium Carbonate → HCID 21071010, compound

HRID 270914Notes

Reaction equation

HRID 270914 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×

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. 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. temperatureThe reaction was 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
  8. customthat on purification on neutral alumina column (pet ether/ethyl acetate)

Sources & evidence

ORD record
ord-f99d1ae9e6834c90837d7d78b2b3459d
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

Loading…