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

HRID 2381997Notes

Reaction equation

HRID 2381997 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.O=[Mn]=O>[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 100%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-methanesulfonyl-indoline (4.11 mmol) and MnO2 (20.55 mmol) in DCM (20 mL) is stirred at rt overnight. The reaction mixture is filtered and the filtrate is concentrated in vacuo to afford 5-methanesulfonyl-1H-indole (782 mg, 100%) as a solid. MS: 196 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.09 (s, 3H), 6.71 (s, H), 7.39 (s, H), 7.53 (d, H), 7.74 (m, H), 8.30 (s, H), 8.66 (br, N—H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-e89fdcac734e49dc8d485d0ccd2597d9
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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