18-Crown-6 → HCID 86658558, compound

HRID 1520204Notes

Reaction equation

HRID 1520204 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14]Br)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[F-:19].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14][F:19])[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 866423312-Bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethanone

Product 1

HCID 86658558HCID 86658558, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 6 Step 1: A solution of 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-bromoethanone (8.39 mmol, 3.00 g), KF (33.6 mmol, 1.97 g) and 18-crown-6 (4.20 mmol, 1.12 g) in acetonitrile (25 mL) was stirred under reflux for 3 hours. After the evaporation of solvent, the crude residue was dissolved in AcOEt. The organic phase was washed with water, was dried over Na2SO4, was filtered and was concentrated. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (100:0 to 95:5) as eluent to yield 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-fluoroethanone (3.62 mmol, 900 mg, 78%) as a white solid.

Workup

  1. temperatureunder reflux for 3 hours
  2. customAfter the evaporation of solvent
  3. dissolutionthe crude residue was dissolved in AcOEt
  4. washThe organic phase was washed with water
  5. dry with materialwas dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated
  8. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-4ce6190fff7a4f37b1ba1b76a7d7e80d
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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