HCID 22024449, compound → HCID 22024336, compound

HRID 1793111Notes

Reaction equation

HRID 1793111 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-1b1c1eafe5ed40898117539f0993ce40
Source dataset
uspto-grants-2006_07
Patent number
US07078405B2

Reaction notes

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