Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-A]pyridine-3-carboxylate → Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1844116Notes

Reaction equation

HRID 1844116 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd].[C]>[OH:8][C:9]1[C:10]2[N:11]([C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 44382335Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-A]pyridine-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 21717316Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

31.45 g (101.3 mmol) of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate were dissolved in 2 l of ethyl acetate, 3.15 g of 10% Pd/carbon were added and the mixture was stirred at RT and atmospheric pressure with hydrogen for 5 h. The mixture was filtered through kieselguhr, the filter cake was washed thoroughly with ethyl acetate/methanol and the filtrate was evaporated to dryness. This gave 21.94 g of the target compound (98% of theory, purity 99%).

Workup

  1. filtrationThe mixture was filtered through kieselguhr
  2. washthe filter cake was washed thoroughly with ethyl acetate/methanol
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-7a3713d8c42546d5bbab45016a2b6626
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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