HCID 22032234, compound → 6-Bromo-8-chloroimidazo[1,2-a]pyridine

HRID 1792455Notes

Reaction equation

HRID 1792455 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:11])[C:5]2[N:6]([CH2:8][CH2:9][N:10]=2)[CH:7]=1>CC(C)=O.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([Cl:11])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 22032234HCID 22032234, compound

Product 1

HCID 220324086-Bromo-8-chloroimidazo[1,2-a]pyridineYield 61.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

2.08 g of 6-bromo-8-chloro-2,3-dihydroimidazo[1,2-a]pyridine was dissolved in 36 mL acetone, and together with 9.1 g of manganese dioxide, the mixture was heated for 9 hours under reflux. The reaction solution was cooled to room temperature, filtered through Celite and washed with ethyl acetate. The solvent was removed, and the resulting crude product was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 1.27 g of the title compound (pale yellow crystals).

Workup

  1. temperatureunder reflux
  2. filtrationfiltered through Celite
  3. washwashed with ethyl acetate
  4. customThe solvent was removed
  5. customthe resulting crude product was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-841344a4b5f34e848713fd145538d083
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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