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

HRID 465997

反応式

HRID 465997 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c7262b43437944ed8a03a8289694a8d5
出典データセット
uspto-grants-1992_10
特許番号
US05155114

関連ノート

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