Methyl iodide → 3-iodo-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine

HRID 633515Notes

Reaction equation

HRID 633515 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[C:6]([O:11][CH3:12])[N:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[CH3:15]I>CN(C)C=O>[I:1][C:2]1[C:10]2[C:5](=[C:6]([O:11][CH3:12])[N:7]=[CH:8][CH:9]=2)[N:4]([CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 534127193-Iodo-7-methoxy-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 903878133-iodo-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodo-7-methoxy-1H-pyrrolo[2,3-c]pyridine (0.75 g, 2.74 mmol) in dimethylformamide (10 mL) was treated with 60% sodium hydride in mineral oil (0.219 g, 5.47 mmol) at room temperature for 20 minutes. To this solution was added methyl iodide (0.505 g, 3.56 mmol). The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 10% ethyl acetate/hexanes to give 0.75 g (95%) of the title compound.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1dd57418a9094f3e8ee3a63fc3515d58
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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