Imidazole → HCID 66961452, compound

HRID 1362605Notes

Reaction equation

HRID 1362605 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5](F)=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH3:18].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>C(OCC)(=O)C.O.CN(C=O)C.CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:18])[C:5]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[C:4]([F:10])[CH:3]=1

Participants

9

Reactant 4

HCID 795ImidazoleHCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 27733075-Bromo-2,3-Difluorophenol

Product 1

HCID 66961452HCID 66961452, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To an acetone (10 mL) solution of 5-bromo-2,3-difluoro phenol (600 μL), potassium carbonate (1.10 g) and iodomethane (654 μL) were added one by one, and the reaction solution was refluxed for 4 hours. The reaction solution was concentrated under reduced pressure and the crude bromo compound was obtained. Potassium carbonate (1.10 g) and imidazole (429 mg) were added to a DMF (10 mL) solution of the obtained bromo compound (1.17 g) one by one, and the reaction solution was agitated at 80° C. overnight. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate=3:1→ethyl acetate:ethanol=10:1), and 510 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. temperaturethe reaction solution was refluxed for 4 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe crude bromo compound was obtained
  4. customthe organic layer was partitioned
  5. washAfter the obtained organic layer was washed with a saturated saline solution, it
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate=3:1→ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record
ord-c2a5469090944a62aeff81699c3ebceb
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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