Iodoethane → HCID 77231185, compound

HRID 1774921Notes

Reaction equation

HRID 1774921 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[CH2:15][CH3:16].[Cl-].[NH4+]>CN(C=O)C.O>[CH2:15]([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)[CH3:16]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 219638871H-Pyrrolo[2,3-b]pyridine-4-carbaldehyde

Product 1

HCID 77231185HCID 77231185, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde (0.413 g, 2.83 mmol) in 5 mL of DMF under an atmosphere of nitrogen was added sodium hydride (74.6 mg, 3.11 mmol). After 5 min, iodoethane (0.529 g, 3.39 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 0-25% ethyl acetate in hexanes to provide 1-ethyl-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 175.2.

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 0-25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-aca2f893eb7e40628cfd35a182361ad8
Source dataset
uspto-grants-2016_02
Patent number
US09260418B2

Reaction notes

Loading…