Methyl iodide → 6-methoxy-3-methylsulfanyl-1H-indole

HRID 23411Notes

Reaction equation

HRID 23411 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([S:12][C:13]#N)=[CH:8][NH:9]2)=[CH:5][CH:4]=1.CI.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([S:12][CH3:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 225741146-methoxy-3-thiocyanato-1H-indole

Product 1

HCID 225740776-methoxy-3-methylsulfanyl-1H-indoleYield 37.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-methoxy-3-thiocyanato-1H-indole (0.336 g, 1.64 mmole) and methyl iodide (0.700 g, 4.93 mmole) in methanol (10 ml) was added potassium hydroxide solution (0.164 ml, 10N) at 0° C. The reaction mixture was stirred for 1 h at room temperature. Silica gel (5 g) was added to the reaction mixture and the solvent was removed under reduced pressure. The residue was purified on a column of silica gel, eluting the product with mixtures of ethyl acetate:hexane (1:9 to 1:1). The first product which was eluted was the desired 6-methoxy-3-methylsulfanyl-1H-indole (0.120 g, 37% yield) followed by 6-methoxy-1H-indole-3-thiol (0.126 g). Step 3

Workup

  1. additionSilica gel (5 g) was added to the reaction mixture
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified on a column of silica gel
  4. washeluting the product with mixtures of ethyl acetate:hexane (1:9 to 1:1)
  5. washThe first product which was eluted

Sources & evidence

ORD record
ord-c6e4ec08a77f4c4ebf36a51163d07893
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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