Acetonitrile → HCID 58244205, compound

HRID 389157Notes

Reaction equation

HRID 389157 reaction equation
C(#N)C.[F:4][C:5]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:6]=1[O:7][C:8]([C:11]1[N:12]([CH3:35])[C:13]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[N:20](CC2C=CC(OC)=CC=2)[CH2:19]3)=[N:14][N:15]=1)([CH3:10])[CH3:9].[N+]([O-])([O-])=O.[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>O>[F:4][C:5]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:6]=1[O:7][C:8]([C:11]1[N:12]([CH3:35])[C:13]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[NH:20][CH2:19]3)=[N:14][N:15]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 9869224Ammonium cerium (IV) nitrateHCID 58243875HCID 58243875, compound

Product 1

HCID 58244205HCID 58244205, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Acetonitrile (25 ml) and water (8.3 ml) were added to 5-{5-[1-(2,4-difluorophenoxy)-1-methylethyl]-4-methyl-4H-1,2,4-triazol-3-yl}-2-(4-methoxybenzyl)isoindolin-1-one (629 mg), and cerium (IV) ammonium nitrate (1.71 g) was added thereto, followed by stirring at room temperature for 2 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:20% methanol-chloroform solution=100:0 to 0:100), the solvent was evaporated under reduced pressure, and the residue was solidified with 2-propanol:diisopropylether (1:1) to obtain, as a colorless powdery solid, 5-{5-[1-(2,4-difluorophenoxy)-1-methylethyl]-4-methyl-4H-1,2,4-triazol-3-yl}isoindolin-1-one (247 mg).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:20% methanol-chloroform solution=100:0 to 0:100)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6b0f284062504ec296cd1291e761f99f
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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