3,5-Dimethylpyrazole → HCID 14449515, compound

HRID 1438341Notes

Reaction equation

HRID 1438341 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-2a466aa4f0bd48a4be924ca05f445309
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

Loading…