Sodium Iodide → HCID 70056084, compound

HRID 1977304Notes

Reaction equation

HRID 1977304 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13](N)=[CH:12][CH:11]=2)[CH:9]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br.C[N:33](C)C=O>O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:28]2[CH2:29][CH2:30][NH:33][CH2:26][CH2:27]2)[CH:9]=1)=[O:4]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6228Dimethylformamide2×HCID 81001,5-Dibromopentane2×HCID 11430Potassium Carbonate2×HCID 57210789Methyl 1-(4-aminophenyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 70056084HCID 70056084, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(4-aminophenyl)-1H-pyrazol-4-carboxylic acid methyl ester (3.0 g) in N,N-dimethylformamide (30 ml) was treated with potassium carbonate (5.72 g), sodium iodide (4.14 g) and 1,5-dibromopentane, and the mixture was stirred for 20 hours at room temperature and 6 hours at 80° C., during which period additional N,N-dimethylformamide (20 ml), 1.5-dibromopentane (1.14 g) and potassium carbonate (0.95 g) were added. The reaction mixture was cooled to room temperature and poured into water. The precipitate was collected by filtration, dried over under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane elution) to give 1-(4-piperidylphenyl)-1H-pyrazol-4-carboxylic acid methyl ester (1.34 g).

Workup

  1. additionwere added
  2. filtrationThe precipitate was collected by filtration
  3. customdried over under reduced pressure
  4. customThe residue was purified by silica gel chromatography (dichloromethane elution)

Sources & evidence

ORD record
ord-5f6656228171466682ef7eae85325d29
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

Loading…