Potassium Carbonate → Ethyl 7-(ethoxymethoxy)imidazo[1,2-a]pyridine-3-carboxylate

HRID 706613Notes

Reaction equation

HRID 706613 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][O:24][CH2:25][CH3:26]>CN(C=O)C>[CH2:25]([O:24][CH2:23][O:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1)[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18523Chloromethyl ethyl etherHCID 178469635HCID 178469635, compound

Product 1

HCID 67976402Ethyl 7-(ethoxymethoxy)imidazo[1,2-a]pyridine-3-carboxylateYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 7-hydroxyimidazo[1,2-a]pyridine-3-carboxylate (100 mg, 0.38 mmol) was dissolved in DMF (3 mL) and treated with potassium carbonate (79 mg, 0.57 mmol). The mixture was stirred at ambient temperature for 30 minutes before adding chloromethylethyl ether (40 mg, 0.42 mmol) and heating mixture to 60° C. for 1 hour. The crude mixture was purified by reverse phase chromatography to give ethyl 7-(ethoxymethoxy)imidazo[1,2-a]pyridine-3-carboxylate (11 mg).

Workup

  1. temperatureheating mixture to 60° C. for 1 hour
  2. customThe crude mixture was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-40c22560350a49788584d20ca21f396f
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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