1-(Imidazo[1,2-a]pyridin-3-yl)ethan-1-one → HCID 59176797, compound

HRID 2238630Notes

Reaction equation

HRID 2238630 reaction equation
[N:1]1[CH:2]=[C:3]([C:10](=[O:12])[CH3:11])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12>COC(OC)N(C)C>[CH3:3][N:4]([CH3:9])/[CH:5]=[CH:11]/[C:10]([C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1)=[O:12]

Participants

3

Reactant 1

HCID 157181821-(Imidazo[1,2-a]pyridin-3-yl)ethan-1-one

Product 1

HCID 59176797HCID 59176797, compound

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

Unpurified imidazo[1,2-a]pyridin-3-ylethanone [1-1] was dissolved in 400 mL of N,N-dimethylformamide dimethylacetal, and overheated overnight under reflux. The dimethylformamide dimethylacetal was distilled off under reduced pressure, and then diethyl ether was added to the residue. Thus obtained solid was separated by filtration and dried under reduced pressure, to obtain 5.06 g of (E)-3-(dimethylamino)-1-imidazo[1,2-a]pyridin-3-yl-2-propen-1-one [1-2] as a light brown solid.

Workup

  1. temperatureoverheated overnight under reflux
  2. distillationThe dimethylformamide dimethylacetal was distilled off under reduced pressure
  3. additiondiethyl ether was added to the residue
  4. customThus obtained solid was separated by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-938b73aebbd24a2eaaab8319abce0f70
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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