Methyl iodide → HCID 18674213, compound

HRID 1635929Notes

Reaction equation

HRID 1635929 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[NH:6][N:5]=1.[CH3:22]I>CN(C)C=O>[NH2:3][C:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:6]([CH3:22])[N:5]=1.[NH2:3][C:4]1[N:5]([CH3:22])[N:6]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 155131015-(4-Fluorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-amine

Product 2

HCID 18674082HCID 18674082, compoundYield 32%HCID 18674213HCID 18674213, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

While a dimethylformamide suspension containing 0.17 g of 60% sodium hydride was being cooled with ice, 10 ml of a dimethylformamide solution containing 1.00 g of 3-amino-5-(4-fluorophenyl)-4-(4-pyridyl)pyrazole was added dropwise thereto, followed by stirring at room temperature for 30 minutes. Then, 5 ml of a dimethylformamide solution containing 0.67 g of methyl iodide was added dropwise thereto, followed by stirring at room temperature for 3 hours. After the dimethylformamide was distilled off under reduced pressure, the resulting residue was extracted with chloroform. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by column chromatography using 250 g of silica gel [with an elution solvent comprising chloroform-methanol (20:1)]. Thus, 0.34 g (32% yield) of 3-amino-5-(4-fluorophenyl)-1-methyl-4-(4-pyridyl)pyrazole (light-brown crystals) was obtained as a first elution product, and 0.45 g (43% yield) of 5-amino-3-(4-fluorophenyl)-1-methyl-4-(4-pyridyl)pyrazole (light-brown crystals) as a second elution product.

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. stirringby stirring at room temperature for 3 hours
  4. distillationAfter the dimethylformamide was distilled off under reduced pressure
  5. extractionthe resulting residue was extracted with chloroform
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-725aec7adf2f4e578161b39580c0be56
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

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