Ethyl chloroformate → 3-(3-Methylpyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 466010

反応式

HRID 466010 の反応式
[C:1]1([C:7]2[CH:15]=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[N:18]=[N:19][CH:20]=[CH:21][CH:22]=1.ClC(OCC)=O>C(Cl)Cl>[CH3:16][C:17]1[N:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:15]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 742083-MethylpyridazineHCID 156203422-Phenylpyrazolo[1,5-a]pyridine

生成物 1

HCID 151581083-(3-Methylpyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine収率 32%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a mixture of 2-phenylpyrazolo[1,5-a]pyridine (5.00 g), 3-methylpyridazine (2.90 g) and methylene chloride (20 ml), was added a solution of ethyl chloroformate (5.57 g) in methylene chloride for 17 minutes under ice-cooling and stirred for an hour at the same temperature and then for 6 hours and 40 minutes at room temperature. To the reaction mixture was added methylene chloride (20 ml), and washed with a solution of potassium carbonate (10 ml) and a saturated aqueous solution of sodium chloride (10 ml) and dried over magnesium sulfate. The solvent was removed and chromatographed on silica gel (70 g) with a mixture of n-hexane and ethyl acetate (2:1). The fractions containing the object compound were combined and evaporated in vacuo and recrystallized from a mixture of ethyl acetate and n-hexane to give 3-(3-methylpyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (2.36 g).

後処理

  1. temperaturecooling
  2. custom40 minutes
  3. customat room temperature
  4. washwashed with a solution of potassium carbonate (10 ml)
  5. dry with materiala saturated aqueous solution of sodium chloride (10 ml) and dried over magnesium sulfate
  6. customThe solvent was removed
  7. customchromatographed on silica gel (70 g) with a mixture of n-hexane and ethyl acetate (2:1)
  8. additionThe fractions containing the object compound
  9. customevaporated in vacuo
  10. customrecrystallized from a mixture of ethyl acetate and n-hexane

出典と根拠

ORDレコード
ord-729fa189f5d6439ca7a86dbb1b294f72
出典データセット
uspto-grants-1992_10
特許番号
US05155114

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