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

HRID 2037840Notes

Reaction equation

HRID 2037840 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 706222-Amino-5-bromopyridine

Product 1

HCID 7141939Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.00 g of 2-amino-5-bromopyridine (3), 16.99 g of ethyl 3-bromo-2-oxopropanoate were dissolved in ethanol (100 mL), and the solution is heated at reflux for 8 hours. The reaction mixture was concentrated, and saturated aqueous NaHCO3 was added to the residue. The resulting precipitate was isolated by filtration, and washed with water to afford 17.01 g of the titled compound as colorless powder (yield: 73%).

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionsaturated aqueous NaHCO3 was added to the residue
  5. customThe resulting precipitate was isolated by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-08cab82af9174561b4e0b03e9ac52327
Source dataset
uspto-grants-2013_11
Patent number
US08575337B2

Reaction notes

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