Ethyl 3-(3-nitropyridin-2-yl)-2-oxopropionate → ethyl 1H-pyrrolo(3,2-b)pyridine-2-carboxylate

HRID 230545Notes

Reaction equation

HRID 230545 reaction equation
[N+:1]([C:4]1[C:5]([CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].C(O)C>[NH:1]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:10]=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 1

HCID 59753617Ethyl 3-(3-nitropyridin-2-yl)-2-oxopropionate

Product 1

HCID 11579250ethyl 1H-pyrrolo(3,2-b)pyridine-2-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

18.4 g of ethyl 3-(3-nitropyridin-2-yl)-2-oxopropionate and 5.5 g of 10% palladium-on-charcoal are added to 500 ml of ethanol, and the reaction mixture is hydrogenated under 2 bar for 3 hours at 20° C. The reaction mixture is then filtered over a thin layer of silica gel and the filtrate is concentrated under reduced pressure, to give 14.1 g of ethyl 1H-pyrrolo[3,2-b]-pyridine-2-carboxylate, the characteristics of which are as follows:

Workup

  1. filtrationThe reaction mixture is then filtered over a thin layer of silica gel
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b18465d06854593b295fc1f4c2fefb1
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

Loading…