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

HRID 1060814Notes

Reaction equation

HRID 1060814 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-9991424f3e2f4b1e884ed923c898baa5
Source dataset
uspto-grants-2003_02
Patent number
US06525070B2

Reaction notes

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