Pyridine → 4-Bromo-1-(4-fluorophenyl)-1H-imidazole

HRID 1823987Notes

Reaction equation

HRID 1823987 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[F:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.N1C=CC=CC=1>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2856454-Fluorophenylboronic acidHCID 178418934HCID 178418934, compound

Product 1

HCID 221480334-Bromo-1-(4-fluorophenyl)-1H-imidazoleYield 37%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-bromo-1H-imidazole (223 mg, 1.52 mmol), 4-fluorophenylboronic acid (425 mg, 3.03 mmol), copper(II) acetate (413 mg, 2.28 mmol), pyridine (0.25 mL) and powdered 4 Å molecular sieves (1 g) in 1,2-dichloroethane (7 mL) was stirred at room temperature under a slow stream of air for 44 hours. The reaction mixture was filtered through Celite®, washing with ethyl acetate. The filtrate was concentrated and the residue purified by flash column chromatography on silica eluting with 10 to 20% ethyl acetate/isohexane to give the product as a white solid (135 mg, 37%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwashing with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by flash column chromatography on silica eluting with 10 to 20% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-9e791cdec0e3496aaf5f044a46f2e285
Source dataset
uspto-grants-2006_05
Patent number
US07041689B2

Reaction notes

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