Ethyl bromopyruvate → HCID 66656352, compound

HRID 2367725Notes

Reaction equation

HRID 2367725 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1>[CH2:16]([O:15][C:13]([C:12]1[N:1]=[C:2]2[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]2[CH:11]=1)=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 70155242-Aminoisonicotinonitrile

Product 1

HCID 66656352HCID 66656352, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-cyanopyridine (4.00 g, 33.6 mmol) in THF (100 mL) add ethyl bromopyruvate (6.55 g, 33.6 mmol). Stir the mixture at rt overnight. A light yellow suspension forms. After filtration and washing with THF, dissolve the light yellow solid in EtOH (50 mL) and heat to reflux for 4 h. Concentrate in vacuo to afford the desired product 7-cyano-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester as a solid (6.21 g, 28.9 mmol).

Workup

  1. filtrationAfter filtration
  2. washwashing with THF
  3. dissolutiondissolve the light yellow solid in EtOH (50 mL)
  4. temperatureheat
  5. temperatureto reflux for 4 h
  6. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-cde48c0c980e4ce6ab0d9ff9ac200d0d
Source dataset
uspto-grants-2014_04
Patent number
US08697911B2

Reaction notes

Loading…