Ethyl (chloroformyl)acetate → Ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

HRID 706609Notes

Reaction equation

HRID 706609 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.Cl[CH:11]([CH:17]=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][N:1]=2)[CH:4]=1)#[N:9]

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 67259960Ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-5-cyanopyridine (15.5 g, 152 mmol) was dissolved in ethanol (500 mL) in 2 L round bottom flask. Ethyl 2-chloro-3-oxopropanoate (5% in benzene; 730 mL; Commercial solution from Toronto Research Chemicals Inc.) was added and the mixture was heated at reflux for 10 hours. The mixture was concentrated under reduced pressure and the residue was purified by silica-gel chromatography to give ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate as a pale yellow solid (13.9 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 10 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-512afadf418e4201bc291138605ce274
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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