N-bromobutanimide → 8-Acetoxy-3-bromo-2-methylimidazo[1,2-a]pyridine

HRID 1871118Notes

Reaction equation

HRID 1871118 reaction equation
[C:1]([O:4][C:5]1[C:6]2[N:7]([CH:11]=[C:12]([CH3:14])[N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Br:15]N1C(=O)CCC1=O>C(O)C.C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:6]2[N:7]([C:11]([Br:15])=[C:12]([CH3:14])[N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 183219268-Acetoxy-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 183218748-Acetoxy-3-bromo-2-methylimidazo[1,2-a]pyridineYield 86.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-acetoxy-2-methylimidazo[1,2-a]pyridine (100 mg) in ethanol (1 ml) was added N-bromosuccinimide (103 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. The mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (ethyl acetate) to give 8-acetoxy-3-bromo-2-methylimidazo[1,2-a]pyridine (123 mg) as oil.

Workup

  1. temperaturecooling
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ab465fad7c0c4172b287edfb65c3b9e9
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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