Acetic Acid → ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 553567Notes

Reaction equation

HRID 553567 reaction equation
[K].[CH3:2][O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([N+:21]([O-])=O)=[CH:9][N:8]=1.C(O)(=O)C.[H][H].C(O)C(F)(F)F>CO.[OH-].[Pd+2].[OH-]>[CH3:2][O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]2[CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:21][C:10]2=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 64092,2,2-TrifluoroethanolHCID 67461922Ethyl 3-[2-(2-methoxyethoxy)-5-nitropyridin-4-yl]-2-oxopropionate potassium saltHCID 178418361HCID 178418361, compound

Product 1

HCID 59820057ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

3.5 g of dried ethyl 3-[2-(2-methoxyethoxy)-5-nitropyridin-4-yl]-2-oxopropionate potassium salt are dissolved in 50 ml of MeOH, and 2 ml of acetic acid are added. After the addition of 500 mg of palladium hydroxide/C 20%, the mixture is stirred under 1 atm of hydrogen. After 5 h, a further 200 mg of catalyst and 0.75 ml of trifluoroethanol are added. After a further 3 h, all volatile components are removed under reduced pressure and 20 ml of sat. sodium bicarbonate solution are added and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:2). This gives ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate as a yellowish solid. C13H16N2O4 (264.28), MS (ESI): 265 (M+H+).

Workup

  1. waitAfter a further 3 h
  2. customall volatile components are removed under reduced pressure and 20 ml of sat. sodium bicarbonate solution
  3. additionare added
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-96fd6bfae9a442b1afffa004dd3bf546
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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