Methanol → Methyl 5-methoxy-1H-pyrrolo[2,3-C]pyridine-2-carboxylate

HRID 245773Notes

Reaction equation

HRID 245773 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[NH:9][C:6]2=[CH:7][N:8]=1.S(=O)(=O)(O)O.[CH3:20]O>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:20])=[O:13])[NH:9][C:6]2=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 177504195-Methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Product 1

HCID 49759101Methyl 5-methoxy-1H-pyrrolo[2,3-C]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1 g, 5.20 mmol) in methanol (100 ml) was added sulfuric acid (0.014 ml, 0.260 mmol). The resulting solution was heated to reflux and stirred at this temperature overnight. Then extra sulfuric acid (0.277 ml, 5.20 mmol) was added and heated at reflux for five days. The heating was stopped and the reaction mixture was concentrated to a smaller volume. The resulting suspension was diluted with ethyl acetate and washed with an aqueous saturated sodium hydrogen carbonate solution. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to give methyl 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (910 mg).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. temperatureheated
  4. temperatureat reflux for five days
  5. concentrationthe reaction mixture was concentrated to a smaller volume
  6. additionThe resulting suspension was diluted with ethyl acetate
  7. washwashed with an aqueous saturated sodium hydrogen carbonate solution
  8. extractionThe aqueous layer was extracted twice with ethyl acetate
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e11d1ae1f0e049ca844fcc4324b54185
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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