Methanol → 1-Benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-imidazole

HRID 2252029Notes

Reaction equation

HRID 2252029 reaction equation
[CH2:1]([N:8]1[C:12](Br)=[C:11]([Br:14])[N:10]=[C:9]1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[C:28]([F:30])[CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].CO>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:12]([C:26]2[CH:25]=[C:24]([F:23])[CH:29]=[C:28]([F:30])[CH:27]=2)=[C:11]([Br:14])[N:10]=[C:9]1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 17981678HCID 17981678, compound

Product 1

HCID 179816431-Benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-imidazoleYield 45.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Reflux a mixture of 1-benzyl-4,5-dibromo-2-(2,4-difluoro-phenyl)-imidazole (0.386 g, 0.90 mmol), 3,5-difluorophenyl boronic acid (0.15 g, 0.945 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (0.065 g, 0.09 mmol), 2 M sodium carbonate (0.90 mL), methanol (1.5 mL) and toluene (10 mL) for 18 hours, then cool to ambient temperature. Dilute with ethyl acetate and wash with saturated sodium bicarbonate, saturated sodium chloride, dry with magnesium sulfate, filter and remove solvents under reduced pressure. Purify the residue on silica gel eluting with hexane/ethyl acetate mixtures to provide 1-benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-1H-imidazole (0.19 g). MS(ES+): m/z=461.0 (M+H)+

Workup

  1. temperatureReflux
  2. washwash with saturated sodium bicarbonate, saturated sodium chloride
  3. dry with materialdry with magnesium sulfate
  4. filtrationfilter
  5. customremove solvents under reduced pressure
  6. customPurify the residue on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-78989c67ce464ad6b92d23ef0e747e0c
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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