Potassium Carbonate → N-(2,6-dimethyl-4-{3,5-dimethylphenyl}phenyl)-2-(4-fluoro phenyl)imidazole

HRID 601695Notes

Reaction equation

HRID 601695 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:4]([CH3:21])[CH:3]=1.[CH3:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([CH3:29])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:8][C:6]1[CH:7]=[C:2]([C:25]2[CH:26]=[C:27]([CH3:29])[CH:28]=[C:23]([CH3:22])[CH:24]=2)[CH:3]=[C:4]([CH3:21])[C:5]=1[N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343493,5-Dimethylphenylboronic acidHCID 68802622N-(4-bromo-2,6-dimethylphenyl)-2-(4-fluorophenyl)imidazole

Product 1

HCID 58750732N-(2,6-dimethyl-4-{3,5-dimethylphenyl}phenyl)-2-(4-fluoro phenyl)imidazoleYield 91.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

8.5 g (24.6 mmol) N-(4-bromo-2,6-dimethylphenyl)-2-(4-fluorophenyl)imidazole, 4.43 g (29.5 mmol) 3,5-dimethylphenylboronic acid, 0.17 g (0.74 mmol) palladium (II) acetate, 9.17 g (66.5 mmol) potassium carbonate and 0.65 g (2.46 mmol) triphenylphosphine were refluxed in 350 mL 1,2-dimethoxyethane and 130 mL water for 18 hours under N2 atmosphere. The cooled mixture was then transferred to a separatory funnel whereupon the water was removed. The organic material was then enriched with ethyl acetate and extracted from water. The organic layer was dried over anhydrous MgSO4, filtered and evaporated of solvent to give a light residue. The residue was then purified on a silica gel column using 50% ethyl acetate/hexanes as eluent. The pure fractions were evaporated of solvent the solids collected on a funnel with hexanes to give 8.34 g N-(2,6-dimethyl-4-{3,5-dimethylphenyl}phenyl)-2-(4-fluoro phenyl)imidazole as a bright white solid. MS confirmed.

Workup

  1. customwas removed
  2. extractionextracted from water
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated of solvent
  6. customto give a light residue
  7. customThe residue was then purified on a silica gel column
  8. customThe pure fractions were evaporated of solvent the solids
  9. customcollected on a funnel with hexanes

Sources & evidence

ORD record
ord-f44e0fa5ec9642d6a79043db62302489
Source dataset
uspto-grants-2011_03
Patent number
US07902374B2

Reaction notes

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