Ethyl bromopyruvate → Ethyl 6-fluoroimidazo[1,2-a]pyridine-2-carboxylate

HRID 349748Notes

Reaction equation

HRID 349748 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(OCC)C>[CH2:15]([O:14][C:12]([C:11]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]2[CH:10]=1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 40148106Ethyl 6-fluoroimidazo[1,2-a]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-amino-5-fluoropyridine (1.12 g) in diethyl ether (25 ml) was added ethyl bromopyruvate (1.25 ml). the mixture was stirred for 1 hour. The resultant solid was filtered off, suspended in ethanol and heated at reflux for 4 hours. The solvent was removed by evaporation and the residue partitioned between ethyl acetate (100 ml) and aqueous sodium bicarbonate solution (100 ml). The organic layer was separated, dried, (magnesium sulfate) and the solvent removed by evaporation. The residue was purified by flash chromatography (silica) eluting with ethyl acetate:hexane (3:1) to give the sub-title compound as a colourless solid (1.12 g).

Workup

  1. filtrationThe resultant solid was filtered off
  2. temperatureheated
  3. temperatureat reflux for 4 hours
  4. customThe solvent was removed by evaporation
  5. customthe residue partitioned between ethyl acetate (100 ml) and aqueous sodium bicarbonate solution (100 ml)
  6. customThe organic layer was separated
  7. customdried
  8. custom(magnesium sulfate) and the solvent removed by evaporation
  9. customThe residue was purified by flash chromatography (silica)
  10. washeluting with ethyl acetate:hexane (3:1)

Sources & evidence

ORD record
ord-4dd1b4c92530425f8f6e2a44d2029e20
Source dataset
uspto-grants-2007_02
Patent number
US07179922B2

Reaction notes

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