Methyl iodide → HCID 178419860, compound

HRID 2231258Notes

Reaction equation

HRID 2231258 reaction equation
C[C:2]1[NH:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[H-].[Na+].CI>CN(C)C=O>[NH:3]1[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=[CH:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178432317HCID 178432317, compound

Product 1

HCID 178419860HCID 178419860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-1H-imidazo[4,5-c]pyridine in 50 ml of dimethylformamide was added 1.43 g of 50% sodium hydride in oil followed, after 20 minutes, by 1.86 ml of methyl iodide. After stirring at room temperature overnight, the solvent was concentrated in vacuo and the residue treated with chloroform and filtered. Removal of the chloroform gave a brown solid which was chromatographed on 150 g of silica gel using 5% methanol in chloroform as the eluent giving 774 mg of a less polar isomer and 356 mg of the desired 1H-imidazo[4,5-c]pyridine isomer.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. additionthe residue treated with chloroform
  3. filtrationfiltered
  4. customRemoval of the chloroform
  5. customgave a brown solid which
  6. customwas chromatographed on 150 g of silica gel using 5% methanol in chloroform as the eluent

Sources & evidence

ORD record
ord-30eac0bbdbe447bfbad8b6a3f7e8a4a6
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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