Ethyl 2-chloroacetoacetate → 8-Amino-6-bromo-3-carboethoxy-2-methylimidazo[1,2-a]pyridine

HRID 1386092Notes

Reaction equation

HRID 1386092 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.Cl[CH:11]([C:17]([CH3:19])=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[NH2:8][C:7]1[C:2]2[N:3]([C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:17]([CH3:19])[N:1]=2)[CH:4]=[C:5]([Br:9])[CH:6]=1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 217173648-Amino-6-bromo-3-carboethoxy-2-methylimidazo[1,2-a]pyridineYield 39.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,3-diamino-5-bromopyridine (2.5 g, 13.31 mmol) and ethyl 2-chloroacetoacetate (2.41 g, 14.64 mmol) in 35 ml abs. Ethanol was refluxed for 14 h. The ethanol was evaporated under reduced pressure. The residue was dissolved in methylene chloride and neutralized by aqueous NaHCO3. The organic layer was separated, dried and evaporated in vacuo. The residue was purified by column chromatography on silica gel with methylene chloride:methanol (100:3.5) as eluent to give 1.55 g (39%) of the title compound.

Workup

  1. customThe ethanol was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with methylene chloride:methanol (100:3.5) as eluent

Sources & evidence

ORD record
ord-5526cfd530954a70820f1d741e08cdee
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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