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

HRID 874435Notes

Reaction equation

HRID 874435 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 ambient 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 ambient 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 chromatography (silica gel, 10% ethyl acetate in hexanes) to afford the title compound (0.75 g, 95%).

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 chromatography (silica gel, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6e83e796de0041d4b2ba59c6109494dc
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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