Ethyl (chloroformyl)acetate → Ethyl 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylate

HRID 1095693Notes

Reaction equation

HRID 1095693 reaction equation
Cl[CH:2]([CH:8]=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=1>CCO>[CH3:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][N:18]2[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:8][N:21]=[C:17]2[CH:16]=1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 667820424-(2-Methoxyethoxy)pyridin-2-amine

Product 1

HCID 66782057Ethyl 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-chloro-3-oxopropanoate (5.1 g, 33.9 mmol, Heterocycles 1991, pg. 699) and 4-(2-methoxyethoxy)pyridin-2-amine (5.70 g, 33.9 mmol) was dissolved in EtOH (50 mL) and heated to reflux overnight. The crude reaction mixture was concentrated and purified by flash column chromatography (EtOAc/MeOH 10:0 to 10:1) provided the desired product (57%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe crude reaction mixture
  4. concentrationwas concentrated
  5. custompurified by flash column chromatography (EtOAc/MeOH 10:0 to 10:1)

Sources & evidence

ORD record
ord-c1b4fdccede64e9ea059f495898ba990
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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