HCID 22024449, compound → HCID 22024336, compound

HRID 501037Notes

Reaction equation

HRID 501037 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:8]([CH2:13]O)=[C:9]([S:11][CH3:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1>CC(C)=O.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[C:3]2[N:4]([C:8]([CH3:13])=[C:9]([S:11][CH3:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22024449HCID 22024449, compound

Product 1

HCID 22024336HCID 22024336, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

The resulting [8-bromo-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]methanol (640 mg) was dissolved in acetone (50 mL), then activated manganese (IV) oxide (4 g) was added thereto, and the mixture was stirred overnight. Manganese (IV) oxide was filtered off through Celite, and the filtrate was evaporated. The resulting residue was purified by column chromatography using silica gel (ethyl acetate:n-hexane=1:10), to give 8-bromo-3-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridine (120 mg) as a brown oil.

Workup

  1. filtrationManganese (IV) oxide was filtered off through Celite
  2. customthe filtrate was evaporated
  3. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-f5b2fe6e04f04944b41f5084fafe5daa
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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