Methyl iodide → methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 245774Notes

Reaction equation

HRID 245774 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[NH:9][C:6]2=[CH:7][N:8]=1.[H-].[Na+].I[CH3:19]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]([CH3:19])[C:6]2=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 49759101Methyl 5-methoxy-1H-pyrrolo[2,3-C]pyridine-2-carboxylate

Product 1

HCID 67366332methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylateYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (910 mg, 4.41 mmol) in N,N-dimethylformamide (35 ml) at room temperature under a nitrogen atmosphere was added slowly sodium hydride (60 w/w % in mineral oil, 177 mg, 4.41 mmol). After 30 minutes iodomethane (0.302 ml, 4.85 mmol) was added and the reaction mixture was stirred at room temperature for 1.5 hours. Then the reaction was quenched in water and extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (gradient of heptane to heptane/ethyl acetate 1/1) to give methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (878 mg).

Workup

  1. customThen the reaction was quenched in water
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (gradient of heptane to heptane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-86b717fbf12545529e3ee9ef336a5eae
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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