Pyridine → 1-(4-Methoxy-3-methylphenyl)-3,4,5-trimethyl-1H-pyrazole

HRID 628506Notes

Reaction equation

HRID 628506 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[CH3:12].[CH3:13][C:14]1[C:18]([CH3:19])=[C:17]([CH3:20])[NH:16][N:15]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:15]2[C:14]([CH3:13])=[C:18]([CH3:19])[C:17]([CH3:20])=[N:16]2)=[CH:5][C:4]=1[CH3:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 1385283,4,5-TrimethylpyrazoleHCID 2773487(4-Methoxy-3-methylphenyl)boronic acid

Product 1

HCID 1182365881-(4-Methoxy-3-methylphenyl)-3,4,5-trimethyl-1H-pyrazoleYield 52.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-methoxy-3-methyl-phenylboronic acid 10 g, 3,4,5-trimethyl-1H-pyrazole (described in Reference Preparation example 49) 7.3 g, copper(II) acetate 18.4 g, pyridine 10.0 g, molecular sieves 4 A 20.0 g and acetonitrile 300 ml was stirred with heating under reflux for thirty hours. The reaction mixture was filtered through Celite and was concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(4-methoxy-3-methyl-phenyl)-3,4,5-trimethyl-1H-pyrazole 7.3 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for thirty hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-68029b310fc04e7cb81d7653f01ece76
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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