Xenon difluoride → trans-N-{[2-(3-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

HRID 1639859Notes

Reaction equation

HRID 1639859 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[N:3]1.[Xe](F)[F:20]>C(#N)C.C(=O)([O-])O.[Na+]>[F:20][C:10]1[N:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[C:8]([C@@H:11]1[CH2:13][C@H:12]1[CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 83674Xenon difluorideHCID 59334573trans-N-{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

Product 1

HCID 59334602trans-N-{[2-(3-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamideYield 6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of trans-N-{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide (400 mg, 1.644 mmol) in acetonitrile (16 mL) was added xenon difluoride (306 mg, 1.808 mmol), and the mixture was stirred under nitrogen atmosphere at room temperature for 4.5 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0), HPLC and TLC to give the title compound (24 mg, yield 6%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0), HPLC and TLC

Sources & evidence

ORD record
ord-20621d4162a94dc9ad4f6466d5ea554c
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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