1,4-Dioxane → 1H-Imidazo[4,5-b]pyridine-2-carbaldehyde

HRID 1175734Notes

Reaction equation

HRID 1175734 reaction equation
[CH:1]([C:3]1[NH:4][C:5]2[C:6]([N:11]=1)=[N:7][CH:8]=[CH:9][CH:10]=2)=C.I([O-])(=O)(=O)=[O:13].[Na+].O1CCOCC1>O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH:1]([C:3]1[NH:4][C:5]2[C:6]([N:11]=1)=[N:7][CH:8]=[CH:9][CH:10]=2)=[O:13]

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 17877573HCID 17877573, compoundHCID 23667635Sodium periodate

Product 1

HCID 5901051H-Imidazo[4,5-b]pyridine-2-carbaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of vinylimidazo[4,5-b]pyridine (1 eq.), osmium tetroxide (0.1 eq.), sodium periodate (3-4 eq.), 1,4-dioxane (30 ml/mmol), and water (25 ml/mmol) is stirred for 15-30 min at ambient temperature. The resulting slurry is diluted with even amounts of water and ethyl acetate. After filtration through Celite®, the organic phase is dried over sodium sulfate, concentrated in vacuo and purified via flash chromatography to yield the respective formylimidazo[4,5-b]pyridine.

Workup

  1. filtrationAfter filtration through Celite®
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified via flash chromatography

Sources & evidence

ORD record
ord-93768bc1f9394ff0929d711da92d2373
Source dataset
uspto-grants-2010_11
Patent number
US07842698B2

Reaction notes

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