Methyl iodide → 1-Methyl-2-(3-pyridyl)indole

HRID 634631Notes

Reaction equation

HRID 634631 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:2]=1.[H-].[Na+].CI.[C:20](=O)([O-])O.[Na+]>CN(C)C=O>[CH3:20][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:7]1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 6066772-(pyridin-3-yl)-1H-indole

Product 1

HCID 103530151-Methyl-2-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under argon, a dimethylformamide (30 ml) solution of 2-(3-pyridyl)indole (3.07 g) was added to dimethylformamide (20 ml) in which 60% sodium hydride (0.76 g) was suspended and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (1.2 ml) was added at 0° C. and the mixture was stirred at room temperature for one hour. The mixture was reacted at 0° C., then a saturated aqueous sodium hydrogencarbonate solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate, then the solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography to obtain 1-methyl-2-(3-pyridyl)indole (1.72 g).

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. customThe mixture was reacted at 0° C.
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3da83e48e86a4a5aa7e7a985846ebf0c
Source dataset
uspto-grants-2001_02
Patent number
US06184238B2

Reaction notes

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