3,5-Dimethylpyrazole → HCID 14449515, compound

HRID 859757Notes

Reaction equation

HRID 859757 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.Br[CH2:11][CH2:12][F:13]>CN(C=O)C.O>[F:13][CH2:12][CH2:11][N:5]1[C:4]([CH3:3])=[CH:8][C:7]([CH3:9])=[N:6]1

Participants

6

Reactant 3

HCID 62103,5-DimethylpyrazoleHCID 129822-Fluoroethyl bromideHCID 24758Sodium hydride

Product 1

HCID 14449515HCID 14449515, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (1.37 mol, (60% in oil) in DMF (350 mL) was added 3,5-dimethyl-1H-pyrazole (120 g, 1.25 mol). After this, the reaction mixture was stirred for 1 h at room temperature and treated with 1-bromo-2-fluoroethane (175 g, 1.37 mol) in DMF (200 mL). The reaction mixture was left to stir overnight, diluted with water (2 L), and the product was extracted with ethyl acetate (3×300 mL). The combined organic extracts were washed with water (1 L), dried with sodium sulfate, and evaporated. The liquid residue (120 g) was chromatographed on a “Biotage” apparatus with silica gel using ethyl acetate/hexane (1:5) as the eluent (Rf=0.3) to give 88 g (49.7%) of the title product.

Workup

  1. waitThe reaction mixture was left
  2. stirringto stir overnight
  3. extractionthe product was extracted with ethyl acetate (3×300 mL)
  4. washThe combined organic extracts were washed with water (1 L)
  5. dry with materialdried with sodium sulfate
  6. customevaporated
  7. customThe liquid residue (120 g) was chromatographed on a “Biotage” apparatus with silica gel

Sources & evidence

ORD record
ord-3fb915ca8c1f47d7b461d0286a376743
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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