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

HRID 706662Notes

Reaction equation

HRID 706662 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[CH:11]=2)[CH2:3][CH2:2]1.Cl[CH:18]([CH:24]=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]3[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][N:16]=[C:12]3[CH:11]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 672520854-(2-Morpholinoethoxy)pyridin-2-amine

Product 1

HCID 67259084Ethyl 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Morpholinoethoxy)pyridin-2-amine (1.37 g, 6.14 mmol) was dissolved in ethanol (20 ml) and treated with ethyl 2-chloro-3-oxopropanoate (5% solution in benzene, 30 mL). The mixture was refluxed overnight. The reaction mixture was cooled and concentrated to afford a beige solid (1.31 g), which was purified by chromatography on silica, eluting with a gradient from 50% EtOAc/Hexanes to 100% EtOAc, followed by 10% MeOH/DCM to provide 1.0 g of the desired product as a white solid.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-05a222769c564f67ac18a0e559dda813
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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