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

HRID 1460320Notes

Reaction equation

HRID 1460320 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-a55749abef2748b09a07935bd0dbd01e
Source dataset
uspto-grants-1991_12
Patent number
US05070205

Reaction notes

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