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

HRID 49396Notes

Reaction equation

HRID 49396 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 purified by column chromatography (silica gel; isocratic 8% ethyl acetate/hexanes) to yield 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. custompurified by column chromatography (silica gel; isocratic 8% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c56a9c2c0b14453491f4ee6570492311
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Reaction notes

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