Magnesium monoxide → 1-(5-Ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridine

HRID 1886191Notes

Reaction equation

HRID 1886191 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([CH3:22])[N:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][N:12]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1.[O-2].[Mg+2]>C(O)C.[Pd]>[CH2:20]([O:19][C:17]([C:14]1[CH:15]=[CH:16][C:11]([N:10]2[C:6]3[CH:5]=[CH:4][N:3]=[CH:2][C:7]=3[N:8]=[C:9]2[CH3:22])=[N:12][CH:13]=1)=[O:18])[CH3:21]

Participants

5

Reactant 2

HCID 6850729Magnesium monoxideHCID 198771824-Chloro-1-(5-ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridine

Product 1

HCID 198771831-(5-Ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-chloro-1-(5-ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridine in ethanol (100 ml) was hydrogenated over 30% palladium on carbon (3 g) and magnesium oxide (0.8 g) at 50 p.s.i. (345 kPa) for 30 hours. The mixture was filtered through Arbocel filter aid and the filter cake washed with boiling ethanol (6×50 ml). The filtrate was concentrated under reduced pressure yielding the title compound as a white foam, (2.75 g, 96%).

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. washthe filter cake washed with boiling ethanol (6×50 ml)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-240cfb2685614d87ae37ebb26045f952
Source dataset
uspto-grants-1992_09
Patent number
US05149814

Reaction notes

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