Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate → ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 2093105Notes

Reaction equation

HRID 2093105 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-])=O>ClCCl.[Pd]>[NH:1]1[C:4]2=[CH:5][N:6]=[CH:7][CH:8]=[C:9]2[CH:10]=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 1

HCID 23269548Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

Product 1

HCID 21819001ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate (1.0 eq) in dichloromethane was added 10% Pd/C (1.5 eq.) under nitrogen atmosphere at 110 psi in an autoclave for 48 hrs. Reaction mixture was filtered through celite and concentrated to get brown solid, which, on purification by column chromatography afforded the desired ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate.

Workup

  1. customReaction mixture
  2. filtrationwas filtered through celite
  3. concentrationconcentrated
  4. customto get brown solid, which
  5. customon purification by column chromatography

Sources & evidence

ORD record
ord-dafef5efb481407d8fff78d552dac176
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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