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

HRID 2192272Notes

Reaction equation

HRID 2192272 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-bb863bffed95482db59c13a3d9c51104
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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