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

HRID 1245569Notes

Reaction equation

HRID 1245569 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]pyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 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 4 h, 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 as a viscous oil. 1H NMR (500 MHz, CDCl3) δ 1.36 (t, J=7.5 Hz, 3H), 2.83 (q, J=7.6 Hz, 2H), 6.88 (t, J=6.8 Hz, 1H), 7.20 (m, 1H), 7.55 (dd, J=8.9, 0.9 Hz, 1H), 8.05 (dd, J=6.9, 1.2 Hz, 1H).

Workup

  1. customethanol was 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-a7bff750276a49d2bbd7449d38440d4f
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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