Pyrazole → 1-(3-Benzyloxy-4-nitrobenzyl)-1H-pyrazole

HRID 660743Notes

Reaction equation

HRID 660743 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([CH2:26]Br)[CH:23]=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC#N>[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([CH:23]=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29])[CH2:26][N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1048Pyrazole2×HCID 11430Potassium Carbonate2×HCID 621150422-Benzyloxy-4-bromomethyl-1-nitrobenzene

Product 1

HCID 688389701-(3-Benzyloxy-4-nitrobenzyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of pyrazole (93 mg, 1.4 mmol), K2CO3 (180 mg, 1.30 mmol) and 2-benzyloxy-4-bromomethyl-1-nitrobenzene (Example 83, step C) (193 mg, 0.599 mmol) in MeCN (5 mL) is stirred at RT for 1 h. Additional pyrazole (500 mg, 7.34 mmol) and K2CO3 (200 mg, 1.45 mmol) are added and the mixture is stirred at RT for an additional 15 h. The mixture is partitioned between EtOAc and water and the organic phase is dried over MgSO4. The solvent is removed under reduced pressure to give the title compound.

Workup

  1. stirringthe mixture is stirred at RT for an additional 15 h
  2. customThe mixture is partitioned between EtOAc and water
  3. dry with materialthe organic phase is dried over MgSO4
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-26b4f1e5cf144935ab2ef037d19cd4c2
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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