HCID 23156194, compound → HCID 23156187, compound

HRID 1890632Notes

Reaction equation

HRID 1890632 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[CH2:18][OH:19])[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[CH:18]=[O:19])[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 23156194HCID 23156194, compound

Product 1

HCID 23156187HCID 23156187, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Compound 13 (2.08 g, 7.04 mmol) was dissolved in chloroform (100 mL), and Manganese(IV) oxide (9.20 g, 0.106 mol) was added to the solution, followed by stirring at room temperature overnight. The unsoluble material was filtered out through Celite, and the filtrate was combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:1) to obtain 3-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)benzaldehyde (2.04 g, quantitative yield).

Workup

  1. filtrationThe unsoluble material was filtered out through Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-e04271e5a20e444b9d3e5478bfbb284f
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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