Pyrazole → 1-(4-Methoxyphenyl)-1H-pyrazole

HRID 2120271Notes

Reaction equation

HRID 2120271 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 1049PyridineHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 122381311-(4-Methoxyphenyl)-1H-pyrazoleYield 62%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Copper (II) acetate (960 mg, 5.28 mmol) was added to a flame-dried flask charged with pyrazole (240 mg, 3.52 mmol), 4-methoxyphenylboronic acid (1.07 g, 7.04 mmol), 4 A molecular sieves (1.35 activated powder), and pyridine (570 μl, 7.04 mmol) in methylene chloride. The reaction was stirred for approximately two days at room temperature and then filtered through diatomaceous earth. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (isocratic 8% ethyl acetate/hexanes) to furnish 381 mg (2.18 mmol, 62% yield) of the title compound. LRMS ([M+H+])=175.2.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by column chromatography (isocratic 8% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f80eb3e24eee489b8045662638711ad1
Source dataset
uspto-grants-2004_02
Patent number
US06689888B2

Reaction notes

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