Water → HCID 22320218, compound

HRID 498000Notes

Reaction equation

HRID 498000 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([NH2:12])=[CH:10][CH:9]=[N:8]1.I[C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([NH:12][C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=[N:8]1

Participants

8

Reactant 4

HCID 962WaterHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 13007948HCID 13007948, compound

Product 1

HCID 22320218HCID 22320218, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.02 g, 37.6 mmol), 2-iodobenzoic acid (9.32 g, 37.6 mmol), copper acetate (II) (0.683 g, 3.76 mmol) and potassium carbonate (5.72 g, 41.4 mmol) in N,N-dimethylformamide (20 mL) was heated under reflux for 1 hour under an argon atmosphere. The solution was allowed to cool to room temperature, and poured into water. The solution was made weakly acidic by the addition of acetic acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (9.45 g, 90% yield).

Workup

  1. temperatureunder reflux for 1 hour under an argon atmosphere
  2. filtrationthe resulting crude crystals were collected by filtration
  3. washThe crystals were washed with water and air
  4. customdried

Sources & evidence

ORD record
ord-077d65577ad44ce9afa1f56169dda018
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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