Xenon difluoride → HCID 178527329, compound

HRID 1882071Notes

Reaction equation

HRID 1882071 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:22][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[CH:24][N:25]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[Xe](F)[F:33].C(=O)([O-])O.[Na+]>C(#N)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:22][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[C:24]([F:33])[N:25]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 83674Xenon difluorideHCID 516892Sodium BicarbonateHCID 68431282HCID 68431282, compound

Product 1

HCID 178527329HCID 178527329, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-imidazol-5-yl)pyridine (0.750 g) in acetonitrile (20 mL) was added xenon difluoride (434 mg), and the mixture was stirred at room temperature for 30 min, and at 0° C. for 63 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-100:0, volume ratio) and preparative thin layer chromatography to give the title compound (0.008 g, yield 1%) as a yellow oil. MS: 456 (MH+).

Workup

  1. waitat 0° C. for 63 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-100:0, volume ratio) and preparative thin layer chromatography

Sources & evidence

ORD record
ord-fe669615edfb4f118593919f4558b825
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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