Triacetoxyperiodinane → 1-[4-chloro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-5-(2-oxoethyl)-1H-pyrrole-3-carboxamide

HRID 238960Notes

Reaction equation

HRID 238960 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH2:14][OH:15])=[CH:11][C:10]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[O:17])=[C:9]2[CH3:29])=[C:4]([C:30]([F:33])([F:32])[F:31])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH:14]=[O:15])=[CH:11][C:10]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[O:17])=[C:9]2[CH3:29])=[C:4]([C:30]([F:31])([F:33])[F:32])[CH:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 452787801-[4-Chloro-2-(trifluoromethyl)phenyl]-5-(2-hydroxyethyl)-2-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide

Product 1

HCID 866586531-[4-chloro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-5-(2-oxoethyl)-1H-pyrrole-3-carboxamideYield 85.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound (1.0 g, 2.0 mmol) of Example 1 in dichloromethane (10 mL), Dess-Martin reagent (1.3 g, 3.0 mmol) was added at 0° C. The reaction temperature was raised to room temperature, and after the mixture was further stirred for 1 hour, it was diluted with ethyl acetate and the organic layer was washed with an aqueous sodium hydrogencarbonate solution, an aqueous sodium thiosulfate solution, water and saturated brine. After the solution was dried with sodium sulfate, it was filtered and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give 1-[4-chloro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-5-(2-oxoethyl)-1H-pyrrole-3-carboxamide (0.85 g, 85%).

Workup

  1. washthe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  2. dry with materialAfter the solution was dried with sodium sulfate, it
  3. filtrationwas filtered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0f6f24331b0345dbb224094bc25a3849
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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