Potassium Carbonate → 4-Chloro-1-(5-ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridine

HRID 1460319노트

반응식

HRID 1460319 반응식
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.Cl[C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[N:10]([C:13]3[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2799611Ethyl 6-chloronicotinateHCID 198771904-Chloro-2-methyl-3H-imidazo[4,5-c]pyridine

생성물 1

HCID 198771824-Chloro-1-(5-ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridine수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Chloro-2-methylimidazo[4,5-c]pyridine described in C.A. 79, 105515f but made by the method of Chem. Pharm. Bull, 12 (8) 866-872 (1964) (3.34 g, 20 mmol), and ethyl 6-chloronicotinate (3.71 g, 26.2 mmol) were dissolved in N,N-dimethylformamide (42 ml). Potassium carbonate (2.76 g, 20 mmol) was added and the reaction was refluxed overnight. The reaction mixture was cooled, the solvent removed under reduced pressure and the crude product purified by flash chromatography eluting with ethyl acetate. Fractions containing product were evaporated and the resulting foam triturated with ether. The solid was filtered and dried under reduced pressure yielding the title compound as a yellow solid (3.2 g, 51%).

후처리

  1. temperaturethe reaction was refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed under reduced pressure
  4. customthe crude product purified by flash chromatography
  5. washeluting with ethyl acetate
  6. additionFractions containing product
  7. customwere evaporated
  8. customthe resulting foam triturated with ether
  9. filtrationThe solid was filtered
  10. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-71d0fce18092421b83b4be0e915e7951
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05070205

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