Bromine → 3-Bromo-2-ethyl-imidazo[1,2-a]pyridine

HRID 1357931Notes

Reaction equation

HRID 1357931 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[CH:11]=1)[CH3:2].[Br:12]Br>C(O)C.O>[Br:12][C:11]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 2

HCID 24408BromineHCID 218319912-Ethylimidazo[1,2-a]pyridine

Product 1

HCID 219127413-Bromo-2-ethyl-imidazo[1,2-a]pyridineYield 66.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2-ethyl-imidazo[1,2-a]pyridine (2.17 g, 14.9 mmol) in ethanol (25 mL) was added bromine (2.0 g, 12.5 mmol) in water (5 mL) dropwise at rt. After stirring at rt for 4h, ethanol was evaporated under reduced pressure. The residue was basified with aqueous sodium bicarbonate and extracted with methylene chloride (3×). The organic phase was washed with brine and dried over anhydrous magnesium sulfate. Concentration followed by flash chromatography eluting with 20 % ethyl acetate in hexanes, followed by 50% ethyl acetate in hexanes afforded the title compound (1.88 g) as a viscous oil.

Workup

  1. customwas evaporated under reduced pressure
  2. extractionextracted with methylene chloride (3×)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration
  6. washeluting with 20 % ethyl acetate in hexanes

Sources & evidence

ORD record
ord-561312f5aed24479b2ebee4db8301ee2
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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