Dimethylformamide → 5-methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 1515614Notes

Reaction equation

HRID 1515614 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Na].CN(C)[CH:14]=[O:15]>CO.[Cu]Br>[CH3:14][O:15][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 5360545SodiumHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridineYield 77.3%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 7, 10 g, 50.8 mmol) in N,N-dimethylformamide (200 mL) and methanol (150 mL) at 25° C. was added sodium (100 g, 185.1 mmol) and copper(I) bromide (14.56 g, 101.5 mmol) under a nitrogen atmosphere. The mixture was then heated at reflux for 5 h. After cooling, the solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (3×300 mL), and washed with a saturated aqueous ammonium chloride solution, brine, and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to afford 5-methoxy-1H-pyrrolo[2,3-b]pyridine (5.8 g, 77.3%) as a light yellow solid: LC/MS m/e calcd for C8H8N2O [M+H]+ 149.17, observed 149.3.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 5 h
  3. temperatureAfter cooling
  4. customthe solvent was removed under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate (3×300 mL)
  6. washwashed with a saturated aqueous ammonium chloride solution, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-468c2c39243c4f15807447f217caee49
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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