Methyl iodide → 1-Methyl-6-(methylthio)-1H-indole

HRID 442747Notes

Reaction equation

HRID 442747 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:14]I>CN(C=O)C>[CH3:14][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([S:2][CH3:1])[CH:11]=2)[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 198489176-(Methylsulfanyl)-1H-indole

Product 1

HCID 539966581-Methyl-6-(methylthio)-1H-indoleYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 6-methylsulfanyl-1H-indole (6.8 g, 42 mmol) in DMF (50 mL) was added to a slurry of NaH (55 mmol) in DMF(10 mL) at 0° C. over a period of 10 minutes. After stirring for 1 hour at 0° C., CH3I (4.0 ml,64 mmol) was added and the mixture stirred for 30 minutes at 0° C., then at room temperature for 1 hour, then poured into ice/H2O and extracted with EtOAc. The organic phase was washed with saturated NaCl solution, dried over MgSO4, filtered and evaporated to give 6.7 g (91.0%) of 1-methyl-6-methylsulfanyl-1H-indole as a yellow oil after flash column chromatography.

Workup

  1. stirringthe mixture stirred for 30 minutes at 0° C.
  2. waitat room temperature for 1 hour
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-08e88a35d97e4956842d2a7a999c2e64
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

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