Hydrochloric Acid → HCID 178505918, compound

HRID 1694792Notes

Reaction equation

HRID 1694792 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=2)([C:11]2[N:12]=[CH:13][NH:14][CH:15]=2)O)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=2)[C:11]2[N:12]=[CH:13][NH:14][CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178519737HCID 178519737, compound

Product 1

HCID 178505918HCID 178505918, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Bis-(3,5-difluoro-phenyl)-(1H-imidazol-4-yl)-methanol (0.5 g, 1.55 mmol) was dissolved in 10 ml ethanol and 0.66 ml of 12M hydrochloric acid was added. The mixture was hydrogenated (5% Pd/C, 0.07 g; 100 bar H2, 100° C.) for 20 h. Then the mixture was filtered through Celite®, and the solvent was evaporated. The residue was partitioned between an aqueous solution of potassium carbonate and ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (silica gel, ethyl acetate) to yield 0.2 g (42%) of 4-[bis-(3,5-difluoro-phenyl)-methyl]-1H-imidazole as a white solid; MS (ISP): 307.1 ((M+H)+.).

Workup

  1. customfor 20 h
  2. filtrationThen the mixture was filtered through Celite®
  3. customthe solvent was evaporated
  4. customThe residue was partitioned between an aqueous solution of potassium carbonate and ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-13f91a7c36be4d26b28da40589c882b1
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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