m-Chloroperbenzoic acid → HCID 53472216, compound

HRID 1182710Notes

Reaction equation

HRID 1182710 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:18]([CH2:19][O:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[C:26](=[O:30])[N:25]([CH2:31][CH2:32][O:33][C:34]([F:37])([F:36])[F:35])[CH2:24]3)=[C:17]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:16]=[C:15]([CH3:44])[N:14]=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:12][C:13]1[C:18]([CH2:19][O:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[C:26](=[O:30])[N:25]([CH2:31][CH2:32][O:33][C:34]([F:37])([F:35])[F:36])[CH2:24]3)=[C:17]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:16]=[C:15]([CH3:44])[N+:14]=1[O-:9]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53472126HCID 53472126, compound

Product 1

HCID 53472216HCID 53472216, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

3-Chloroperbenzoic acid (19.3 mg, 0.112 mmol) was added to a solution of 5-((2,6-dimethyl-4-phenylpyridin-3-yl)methoxy)-2-(2-(trifluoromethoxy)-ethyl)isoindolin-1-one (40 mg, 0.074 mmol, 85% pure) in DCM. After stiffing overnight the reaction mixture was diluted with DCM, sat. aqueous NaHCO3 solution was added. Extraction with DCM, washing of the combined organic layers with water, drying over MgSO4 followed by purification by HPLC provided 2,6-dimethyl-3-((1-oxo-2-(2-(trifluoromethoxy)ethyl)-isoindolin-5-yloxy)methyl)-4-phenylpyridine 1-oxide (23 mg, 64%). ESI-MS [M+H]+=473.1.

Workup

  1. additionwas added
  2. extractionExtraction with DCM
  3. washwashing of the combined organic layers with water
  4. dry with materialdrying over MgSO4
  5. customfollowed by purification by HPLC

Sources & evidence

ORD record
ord-2083eb28b60344989bc64bcee0584b63
Source dataset
uspto-grants-2014_03
Patent number
US08664214B2

Reaction notes

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