2-Aminopyridine → Ethyl 2-{imidazo[1,2-a]pyridin-2-yl}acetate

HRID 920889Notes

Reaction equation

HRID 920889 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17]>C1COCC1>[N:17]1[C:3]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:2][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 10822054Ethyl 2-{imidazo[1,2-a]pyridin-2-yl}acetateYield 26.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-chloro-3-oxobutanoate (15 g, 91 mmol) and pyridin-2-amine (8.58 g, 91 mmol) in THF (80 mL) was refluxed overnight. Then, the reaction mixture was concentrated and the residue purified by silica gel chromatography (PE:EA=1:1) to afford ethyl 2-(imidazo[1,2-a]pyridine-2-yl)acetate (5 g, yield 26.9%).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThen, the reaction mixture was concentrated
  3. customthe residue purified by silica gel chromatography (PE:EA=1:1)

Sources & evidence

ORD record
ord-7b93b53e52ec4803bd59b139e99b82b8
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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