5-(Methanesulfonyl)-2,3-dihydro-1H-indole → 5-(Methylsulfonyl)-1H-indole

HRID 1749931Notes

Reaction equation

HRID 1749931 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH2:9][CH2:8]2)(=[O:4])=[O:3]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 27361365-(Methanesulfonyl)-2,3-dihydro-1H-indole

Product 1

HCID 149732305-(Methylsulfonyl)-1H-indoleYield 71.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 5-(methylsulfonyl)indoline (0.213 g, 1.08 mmol) in chloroform (4 mL) was added with manganese dioxide (0.939 g, 10.8 mmol), and the mixture was stirred at room temperature for 9 hours. The reaction mixture was filtered through Celite, and the resulting filtrate was concentrated to obtain 5-(methylsulfonyl)-1H-indole (0.151 g, 71%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-1b8962c90d08464d995d6db8721b1993
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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