m-Chloroperbenzoic acid → 3-(4-methoxyphenyl)-1-(2-(methylsulfinyl)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole

HRID 240864Notes

Reaction equation

HRID 240864 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:28]3[C:23](=[CH:24][C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=4)=[CH:26][CH:27]=3)[N:22]([C:38]3[CH:43]=[CH:42][N:41]=[C:40]([S:44][CH3:45])[N:39]=3)[CH:21]=2)=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:28]3[C:23](=[CH:24][C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=4)=[CH:26][CH:27]=3)[N:22]([C:38]3[CH:43]=[CH:42][N:41]=[C:40]([S:44]([CH3:45])=[O:6])[N:39]=3)[CH:21]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 509919243-(4-methoxyphenyl)-1-(2-(methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole

Product 1

HCID 509919253-(4-methoxyphenyl)-1-(2-(methylsulfinyl)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indoleYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (m-CPBA; 70%, 95 mg, 0.384 mmol) was added to a mixture solution of 3-(4-methoxyphenyl)-1-(2-(methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (90 mg, 0.192 mmol) in methylene chloride (10 mL) at 0° C. 2 hours later, after adding saturated sodium bicarbonate aqueous solution at 0° C., the mixture was extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The target compound (90 mg) was obtained as white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe collected organic layer was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. dry with materialby drying with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-89cbe88fd252404892cda266402014f2
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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