Imidazole → HCID 22316828, compound

HRID 497204Notes

Reaction equation

HRID 497204 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([C:30]([F:33])([F:32])[F:31])[CH:16]=2)=[CH:11][CH:10]=1.O>CN(C=O)C.[Cu]>[N:3]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:19]([C:20]4[CH:21]=[CH:22][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][CH:25]=4)[N:18]=[C:17]([C:30]([F:32])([F:31])[F:33])[CH:16]=3)=[CH:11][CH:10]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 15340994HCID 15340994, compound

Product 1

HCID 22316828HCID 22316828, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a suspention of sodium hydride (0.04 g: 1 mmol) (60% mineral oil dispersion; washed with dry hexane (3 mL)) in DMF (2 mL) was added imidazol (0.068 g) at room temperature and the mixture was stirred 0.30 minutes. Then, 4-[5-[4-Bromophenyl]-3-trifluoromethyl-1-[4-(methylsulfonyl)phenyl]-1H-pyrazole (0.445 g) and copper powder (0.0063 g) were added and the whole was heated at 150° C. for 3 hours. After cooling, water (30 mL) was added to the reaction mixture and the whole was extracted with CH2Cl2 (30 mL×2), the extract was washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/methanol (1/0.03). The resulting solid was recrystallized with dichloroethane-diisopropyl ether to give the title compound (0.07 g).

Workup

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with CH2Cl2 (30 mL×2)
  3. washthe extract was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/methanol (1/0.03)
  8. customThe resulting solid was recrystallized with dichloroethane-diisopropyl ether

Sources & evidence

ORD record
ord-2b98ac91542c42daa663252c69666913
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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