3,5-Dimethylpyrazole → HCID 14449515, compound

HRID 2387149Notes

Reaction equation

HRID 2387149 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-c5d025337dd44464ac6cf3eaaa35cbc2
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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