Chlorosuccinimide → 3-Carbethoxy-5-chloromethylimidazo[1,2-a]pyridine

HRID 619538노트

반응식

HRID 619538 반응식
[C:1]([C:6]1[N:10]2[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[Cl:16]N1C(=O)CCC1=O.FC(F)(F)C(O)=O.C(OCC)(=O)C>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[C:1]([C:6]1[N:10]2[C:11]([CH2:15][Cl:16])=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2]

참가 물질

6

반응물 3

HCID 31398ChlorosuccinimideHCID 11816548Ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxylateHCID 86754554Trifluoroacetic acid ethyl acetate

생성물 1

HCID 108575483-Carbethoxy-5-chloromethylimidazo[1,2-a]pyridine수율 71.2%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution prepared by dissolving 430 mg (2.06 mM) of 3-carbethoxy-5-methylimidazo[1,2-a]pyridine in 10 ml of ethyl acetate was added 330 mg (2.67 mM) of N-chlorosuccinimide. Then, 1.03 ml (1.03 mM) of 1N-tri-fluoroacetic acid-ethyl acetate was added dropwise at room temperature. The mixture was stirred under argon gas at room temperature for 14 hours. After the reaction, the reaction mixture was poured in 30 ml of saturated aqueous NaHCO3 solution with ice-cooling and the mixture was extracted with 20 ml of ethyl acetate. The organic layer was washed with 30 ml of saturated aqueous NaCl solution and dried over MgSO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate) to provide 350 mg (yield 71.2%) of the title compound as yellow liquid.

후처리

  1. customTo a solution prepared
  2. customAfter the reaction
  3. temperaturecooling
  4. extractionthe mixture was extracted with 20 ml of ethyl acetate
  5. washThe organic layer was washed with 30 ml of saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

출처 및 근거

ORD 기록
ord-baab5c16d39643caa6589dfdaa542212
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958942

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