Ethyl bromopyruvate → Ethyl 6-Cyanoimidazo[1,2-a]pyridine-2-carboxylate

HRID 2080772Notes

Reaction equation

HRID 2080772 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[CH2:10]([O:12][C:13](=[O:18])[C:14](=O)[CH2:15]Br)[CH3:11].C(=O)([O-])O.[Na+]>C(O)C.Cl.CO>[CH2:10]([O:12][C:13]([C:14]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]2[CH:15]=1)=[O:18])[CH3:11]

Participants

6

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 10512851Ethyl 6-Cyanoimidazo[1,2-a]pyridine-2-carboxylateYield 88.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

In ethanol (30 ml), 2-amino-5-cyanopyridine (2.45 g) was dissolved. The solution was added with 3-bromo-2-oxo-propionic acid ethyl ester (3.90 g) and the whole was refluxed under heating for 7 hours. The concentrated residue was dissolved in a minimum amount of a 10% hydrogen chloride/methanol solution and the solution was adjusted to pH 8 with a saturated aqueous sodium hydrogen carbonate solution. The precipitate was collected by filtration, thereby obtaining the subject compound (3.81 g) as a pale-yellow solid.

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 7 hours
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4f5d1c9bbe5942f3aa3d1122877bc650
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…