(7-Methoxy-1H-indol-3-yl)-dimethyl-sulfonium chloride → 7-methoxy-3-methylsulfanyl-1H-indole

HRID 23380Notes

Reaction equation

HRID 23380 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[S+:13](C)[CH3:14]>CS(C)=O>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[S:13][CH3:14]

Participants

3

Reactant 1

HCID 22573983(7-Methoxy-1H-indol-3-yl)-dimethyl-sulfonium chloride

Product 1

HCID 225741157-methoxy-3-methylsulfanyl-1H-indoleYield 87.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(7-Methoxy-1H-indol-3-yl)-dimethyl-sulfonium chloride (0.742 g) prepared in the manner described in Step 1 above was dissolved in DMSO (3 ml) and placed under reduced pressure (house vacuum, ca. 20-50 torr) in a round-bottom flask. The flask was placed on a steam bath and heated until the bubbling stopped. When no more starting material was present, the reaction mixture was cooled and partitioned between ether and water. The organic layer was dried and filtered and then evaporated to dryness to afford 7-methoxy-3-methylsulfanyl-1H-indole (0.514 g, 87.5%).

Workup

  1. customplaced under reduced pressure (house vacuum, ca. 20-50 torr) in a round-bottom flask
  2. customThe flask was placed on a steam bath
  3. temperatureheated until the bubbling
  4. temperaturethe reaction mixture was cooled
  5. custompartitioned between ether and water
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-0313e01f608f4c7bb8da78f078c1e2b2
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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