N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamide → 6-ethyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 645366Notes

Reaction equation

HRID 645366 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([CH:18]=[CH2:19])=[CH:14][N:13]3[CH:20]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CO.[Pd]>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]2[N:13]([CH:20]=[C:10]([C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])[N:11]=2)[CH:14]=1)[CH3:19]

Participants

5

Reactant 2

HCID 24771613N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 247716146-ethyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamideYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 60 mg of N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamide in 15 ml of methanol is hydrogenated at 25° C. for 45 minutes under 1 bar of hydrogen in the presence of 24 mg of 10% palladium-on-charcoal. As the reaction is incomplete, the product is recycled under the same conditions. After filtering, the reaction mixture is concentrated to dryness under reduced pressure. The residue is taken up in 50 ml of ethyl acetate. The organic phase is washed with water, separated by settling, dried and concentrated to dryness under reduced pressure to give 60 mg of 6-ethyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. filtrationAfter filtering
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  3. washThe organic phase is washed with water
  4. customseparated
  5. customdried
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-59f0bdf5cc2e4e1bbbf01be03e22a18e
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

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