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

HRID 433065Notes

Reaction equation

HRID 433065 reaction equation
BrC1C=CC=CC=1CN1[C:13]2[C:8](=[N:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)C=C1.C[O-].[Na+].C[N:24]([CH3:27])[CH:25]=O>CO.[Cu]Br>[CH3:15][O:14][C:10]1[CH:11]=[C:12]2[CH:13]=[CH:8][NH:9][C:27]2=[N:24][CH:25]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 178207361-(2-Bromobenzyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 887MethanolSolvent

Procedure

Under an argon atmosphere and in an anhydrous medium, 1 g (5.07 mmol) of the compound obtained in Step C is dissolved in a mixture of 25 ml of N,N-dimethylformamide and 22 ml of methanol; 6.86 g (126.75 mmol) of sodium methanolate and 1.43 g (10.30 mmol) of copper (I) bromide are added at room temperature. The mixture is heated at reflux for 3 hours. After removal of the solvents by evaporation, the residue is taken up in water and ethyl acetate and then filtered over Celite. The organic phase is washed with water, dried over magnesium sulphate and evaporated to yield a solid, which is purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 7:3). The title compound is obtained in the form of a brown solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. customAfter removal of the solvents
  4. customby evaporation
  5. filtrationethyl acetate and then filtered over Celite
  6. washThe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customto yield a solid, which
  10. customis purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-843f319a378e44edb794298f1c3daf59
Source dataset
uspto-grants-2003_12
Patent number
US06667304B2

Reaction notes

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