Pyrazole → Ethyl 4-(1H-pyrazol-1-YL)benzoate

HRID 1751918Notes

Reaction equation

HRID 1751918 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.I[C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1>>[CH2:14]([O:13][C:11](=[O:12])[C:10]1[CH:16]=[CH:17][C:7]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:8][CH:9]=1)[CH3:15]

Participants

3

Reactant 2

HCID 1048PyrazoleHCID 142891Ethyl 4-iodobenzoate

Product 1

HCID 973146Ethyl 4-(1H-pyrazol-1-YL)benzoate

Procedure

Following General Procedure A (90° C., 30 hours), 1H-pyrazole (205 mg, 3.0 mmol) is coupled with ethyl 4-iodobenzoate (336 μL, 2.0 mmol). The crude brown oil is purified by flash chromatography on silica gel (eluent: dichloromethane/hexanes=80/20) to provide 400 mg (93% isolated yield) of the desired product as a white solid.

Workup

  1. customThe crude brown oil is purified by flash chromatography on silica gel (eluent: dichloromethane/hexanes=80/20)
  2. customto provide

Sources & evidence

ORD record
ord-e6910f2459794195ba32d370454e564f
Source dataset
uspto-grants-2015_10
Patent number
US09162953B2

Reaction notes

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