Methyl iodide → 1-methyl-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde

HRID 82464Notes

Reaction equation

HRID 82464 reaction equation
[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].I[CH3:15].[Cl-].[NH4+]>CN(C=O)C.O>[CH3:15][N:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 219638871H-Pyrrolo[2,3-b]pyridine-4-carbaldehyde

Product 1

HCID 577429851-methyl-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde (0.252 g, 1.72 mmol) in 1 mL of DMF under an atmosphere of nitrogen was added sodium hydride (45.5 mg, 1.90 mmol). After 5 min, iodomethane (0.13 mL, 2.1 mmol) was added. After 30 min, the reaction was treated with saturated aqueous ammonium chloride, diluted with water, and extracted 2× with dichloromethane. The combined organic solution was washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes to provide 1-methyl-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 161.2.

Workup

  1. waitAfter 30 min
  2. extractionextracted 2× with dichloromethane
  3. washThe combined organic solution was washed 3× with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via silica gel chromatography
  8. washeluting with 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-714f7db371f14597954bde496083ef87
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

Loading…