m-Chloroperbenzoic acid → HCID 67204402, compound

HRID 1615383Notes

Reaction equation

HRID 1615383 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=4)[CH:16]=3)[CH:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:32].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[N:8]=[C:7]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=4)[CH:16]=3)[CH:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1)=[O:32]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 58159630HCID 58159630, compound

Product 1

HCID 67204402HCID 67204402, compoundYield 107.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-(Methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (91 mg, 0.251 mmol) was dissolved in methylene chloride (1 mL). At 0° C., 3-chloroperoxybenzoic acid (87 mg, 0.502 mmol) was added. 1 hour later, the reaction mixture was added to sodium bicarbonate aqueous solution and extracted with methylene chloride. The combined organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure. 1-(2-(Methylsulfinyl)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (102 mg) was yielded.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97186357d5594aaeb8a25617147e62cd
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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