Pyrazole → 2-Benzyloxy-4-pyrazol-1-yl-benzonitrile

HRID 1271518Notes

Reaction equation

HRID 1271518 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[CH2:8]([O:15][C:16]1[CH:23]=[C:22](F)[CH:21]=[CH:20][C:17]=1[C:18]#[N:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[CH2:8]([O:15][C:16]1[CH:23]=[C:22]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH:21]=[CH:20][C:17]=1[C:18]#[N:19])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 210698282-(Benzyloxy)-4-fluorobenzonitrile

Product 1

HCID 184528912-Benzyloxy-4-pyrazol-1-yl-benzonitrileYield 74.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 0.180 g pyrazole in 5 mL DMF is added 0.105 g NaH. After stirring 50 minutes at room temperature, 0.200 g of the material from Step A, above, is added all at once with 5 mL DMF. After 2 hours at room temperature, the reaction is quenched with water and Concentrated in vacuo. The residue is redissolved in ethyl acetate and washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography eluting with toluene provides 0.181 g (74.8%) of the title compound.

Workup

  1. waitAfter 2 hours at room temperature
  2. customthe reaction is quenched with water
  3. concentrationConcentrated in vacuo
  4. dissolutionThe residue is redissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washFlash chromatography eluting with toluene

Sources & evidence

ORD record
ord-04f61bef712d4954b85402cb33b9f3ba
Source dataset
uspto-grants-2007_04
Patent number
US07205313B2

Reaction notes

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