Xenon difluoride → N-{2-[(8S)-1-fluoro-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl]ethyl}acetamide

HRID 887817Notes

Reaction equation

HRID 887817 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]3[CH2:13][CH2:12][C@@H:11]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:8]=32)=[N:3]1.[Xe](F)[F:21]>C(#N)C.C(OCC)(=O)C>[F:21][C:10]1[N:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[C:8]1[C@H:11]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH2:12][CH2:13][C:7]=1[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 83674Xenon difluorideHCID 59145842N-{2-[(8S)-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl]ethyl}acetamide

Product 1

HCID 59145893N-{2-[(8S)-1-fluoro-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl]ethyl}acetamideYield 8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{2-[(8S)-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl]ethyl}acetamide (1.01 g, 3.91 mmol) in acetonitrile (39.2 mL) was added xenon difluoride (728 mg, 4.30 mmol) under ice-cooling, and the mixture was stirred for 18 hr. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0) and preparative TLC (methanol/ethyl acetate=10/90) to give the title compound (86.4 mg, yield 8.0%).

Workup

  1. temperaturecooling
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution and 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) and preparative TLC (methanol/ethyl acetate=10/90)

Sources & evidence

ORD record
ord-0fe139d4fba54b9ab84b60e60a2afeff
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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