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

HRID 1292755노트

반응식

HRID 1292755 반응식
[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]

참가 물질

4

반응물 2

HCID 66144Ethyl bromopyruvateHCID 27377012-Amino-5-fluoropyridine

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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 hrs. 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 with MgSO4, 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).

후처리

  1. filtrationThe resultant solid was filtered off
  2. temperatureheated
  3. temperatureat reflux for 4 hrs
  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. dry with materialdried with MgSO4
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by flash chromatography (silica)
  10. washeluting with ethyl acetate:hexane (3:1)

출처 및 근거

ORD 기록
ord-cba487cb080f4df59538876e7b485b9e
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238691B2

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