Imidazo[1,2-a]pyridin-2-ylmethanol → Imidazo(1,2-a)pyridine-2-carbaldehyde

HRID 1772035Notes

Reaction equation

HRID 1772035 reaction equation
[N:1]1[C:2]([CH2:10][OH:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12>CCO.[O-2].[Mn+4].[O-2]>[NH3:1].[OH2:11].[N:1]1[C:2]([CH:10]=[O:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 1

HCID 2795540Imidazo[1,2-a]pyridin-2-ylmethanol

Product 2

HCID 4961257Imidazo(1,2-a)pyridine-2-carbaldehydeYield 30.8%HCID 12896473Azane;hydrateYield 0.01%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of imidazo[1,2-a]pyridin-2-ylmethanol (3.0 g, 20 mmol) in EtOH (50 mL) was added manganese (IV) oxide (8.8 g, 100 mmol). The mixture was refluxed for 2 days. After cooling to room temperature, the mixture was filtered through Celite, and the filtrate was concentrated. The residue was purified by reverse phase column chromatography (eluting with acetonitrile in water 25% v/v, with 0.01% NH3.H2O) to afford the title compound (0.45 g, 15% yield) as a yellow solid. ESI MS: m/z 147 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed for 2 days
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by reverse phase column chromatography (
  5. washeluting with acetonitrile in water 25% v/v

Sources & evidence

ORD record
ord-f1a56ae2a061441bbe4589d52fdcfbbb
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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