m-Chloroperbenzoic acid → HCID 58305588, compound

HRID 2280297Notes

Reaction equation

HRID 2280297 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=3)=[CH:12][CH:11]=[C:10]2[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:5]([CH3:29])[CH:4]=1)#[N:2].C1C=C(Cl)C=C(C(OO)=[O:38])C=1>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([CH3:21])=[O:38])=[CH:16][CH:15]=3)=[CH:12][CH:11]=[C:10]2[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:5]([CH3:29])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58305617HCID 58305617, compound

Product 1

HCID 58305588HCID 58305588, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 3-(1-(4-cyano-2-methylphenyl)-5-(4-(methylthio)phenyl)-1H-pyrrol-2-yl)propanoate (23A) (98 mg, 0.23 mmol) in DCM (1 mL) was added m-CPBA below 0° C. by five portions. Then the reaction mixture was stirred at room temperature for 3 h. TLC showed that the reaction was complete. The mixture was diluted with DCM (10 mL) and washed with sat. NaHCO3 (15 mL), dried over Na2SO4, filtered and concentrated to afford a yellow oil, which was purified by silica gel column chromatography to afford ethyl 3-(1-(4-cyano-2-methylphenyl)-5-(4-(methylsulfinyl)phenyl)-1H-pyrrol-2-yl)propanoate (23B) as a light yellow solid (65 mg, 65%).

Workup

  1. washwashed with sat. NaHCO3 (15 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a yellow oil, which
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3acf3f5f32204e24b7bfe5fa5807493f
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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