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

HRID 748047Notes

Reaction equation

HRID 748047 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([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[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 47%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(4-Methoxyphenyl)-1H-pyrazole was prepared as described in the literature (Tetrahedron Lett. 39 (1998) 2941-2944). To pyrazole (1.0 g, 14.7 mmol) dissolved in a reaction vessel containing CH2Cl2 (100 mL) and 4 Å molecular sieves (6.0 g) was added 4-methoxyphenylboronic acid (4.5 g, 29.4 mmol), pyridine (3 mL, 36.7 mmol) and copper (II) acetate (4.0 g, 22.0 mmol). The reaction mixture was stirred at room temperature for 72 h and then filtered through a plug of Celite. The filtrate was concentrated in vacuo and then purified by flash chromatography (SiO2, EtOAc/hexane, 1:9, then 1:4) to afford a clear oil in 47% yield.

Workup

  1. filtrationfiltered through a plug of Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by flash chromatography (SiO2, EtOAc/hexane, 1:9
  4. custom1:4) to afford a clear oil in 47% yield

Sources & evidence

ORD record
ord-eebc4fb29ba2444b984b3e1ed772f2c6
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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