Xenon difluoride → HCID 178450385, compound

HRID 1881958Notes

Reaction equation

HRID 1881958 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:19][C:20]([C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])=[CH:21][N:22]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Xe](F)[F:29]>C(#N)C.C(OCC)(=O)C>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:19][C:20]([C:23](=[O:27])[CH:24]([CH3:25])[CH3:26])=[C:21]([F:29])[N:22]=2)[C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 83674Xenon difluorideHCID 593312831-(2-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-1H-imidazol-5-yl)-2-methylpropan-1-one

Product 1

HCID 178450385HCID 178450385, compoundYield 13.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (13 mL) of 1-(2-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-1H-imidazol-5-yl)-2-methylpropan-1-one (0.507 g) in acetonitrile was added xenon difluoride (0.440 g), and the mixture was heated under reflux for 4 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60, volume ratio) and recrystallized from diethyl ether-hexane to give the title compound (0.07 g, yield 13%) as colorless crystals. melting point 161-162° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60, volume ratio)
  7. customrecrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-a469996797344009ae53ed746053ceab
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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