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

HRID 703969ノート

反応式

HRID 703969 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-1b8fad8c32fd46e18cdac9cda1d9d6a2
出典データセット
uspto-grants-1991_01
特許番号
US04985444

反応ノート

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