Ethyl bromopyruvate → Ethyl 7-bromoimidazo(1,2-a)pyridine-2-carboxylate

HRID 1943994Notes

Reaction equation

HRID 1943994 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(#N)C>[Br:8][C:6]1[CH:5]=[CH:4][N:3]2[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:1]=[C:2]2[CH:7]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 51063904Ethyl 7-bromoimidazo(1,2-a)pyridine-2-carboxylateYield 56.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.6 g (3.47 mmol) of 2-amino-4-bromopyridine, 1.55 g (7.15 mmol) of ethyl bromopyruvate and 4 mL of acetonitrile are placed in a 20 mL screw-topped tube equipped with a magnetic bar. The top is then screwed on and the tube is stirred at room temperature for 1 hour, and then heated at 150° C. with stirring for 30 minutes. After this time and cooling to room temperature, the precipitate obtained is filtered off, rinsed with acetonitrile and dried. The filtrate is concentrated to dryness and then purified by chromatography on a column of silica gel, eluting with a mixture of dichloromethane and methanol. The solid obtained after evaporating off the solvent is dried under reduced pressure. 530 mg of the expected product are obtained in total.

Workup

  1. customequipped with a magnetic bar
  2. temperatureheated at 150° C.
  3. stirringwith stirring for 30 minutes
  4. temperatureAfter this time and cooling to room temperature
  5. customthe precipitate obtained
  6. filtrationis filtered off
  7. washrinsed with acetonitrile
  8. customdried
  9. concentrationThe filtrate is concentrated to dryness
  10. custompurified by chromatography on a column of silica gel
  11. washeluting with a mixture of dichloromethane and methanol
  12. customThe solid obtained
  13. customafter evaporating off the solvent
  14. customis dried under reduced pressure

Sources & evidence

ORD record
ord-18d80901c6aa4b5bb4355b2d209e8ecc
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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