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

HRID 1085145Notes

Reaction equation

HRID 1085145 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-b36b3706b6ba43eebc8cd5aeaa0f4473
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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