Pyridazine → 3-(1-Ethoxycarbonyl-1,4-dihydropyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 465997

반응식

HRID 465997 반응식
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[C:7]1([C:13]2[CH:21]=[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]3[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1>C(Cl)Cl>[CH2:5]([O:4][C:2]([N:22]1[CH:27]=[CH:26][CH:25]([C:21]2[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:14][N:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=23)[CH:24]=[N:23]1)=[O:3])[CH3:6]

참가 물질

5

반응물 3

HCID 9259PyridazineHCID 10928Ethyl chloroformateHCID 156203422-Phenylpyrazolo[1,5-a]pyridine

생성물 1

HCID 117918603-(1-Ethoxycarbonyl-1,4-dihydropyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine수율 53.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
10 °C

실험 절차

Ethyl chloroformate (3.38 g) was added dropwise with stirring to a solution of 2-phenylpyrazolo[1,5-a]pyridine (2.54 g) and pyridazine (5.00 g) in methylene chloride (5.0 ml) at 10° C. After being stirred at 10° C. for 1 hour and then at room temperature for 2 hours, the reaction mixture was poured onto ice-water (100 ml), and extracted with ethyl acetate. The combined extracts were washed with saturated sodium chloride aqueous solution (100 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (150 g) with a mixture of chloroform and n-hexane (1:1) as an eluant. The fractions containing main-product [compound (A)] were combined and evaporated in vacuo to give 3-(1-ethoxycarbonyl-1,4-dihydropyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (2.42 g).

후처리

  1. waitat room temperature for 2 hours
  2. additionthe reaction mixture was poured onto ice-water (100 ml)
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with saturated sodium chloride aqueous solution (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel (150 g) with a mixture of chloroform and n-hexane (1:1) as an eluant
  8. additionThe fractions containing main-product [compound (A)]
  9. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-c7262b43437944ed8a03a8289694a8d5
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155114

연결된 노트

불러오는 중…