p-Toluenesulfonic acid → 7-bromo-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazole

HRID 902554

反応式

HRID 902554 の反応式
[Br:1][C:2]1[C:10]2[C:6](=[C:7]([C:12](O)([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:10]2[C:6](=[C:7](/[C:12](/[CH2:16][CH2:17][CH3:18])=[CH:13]/[CH2:14][CH3:15])[N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 210945894-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol

生成物 1

HCID 597023557-bromo-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazole収率 89%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 4-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol (1.75 g, 5.38 mmol), 50 mL of toluene, and 4-toluenesulfonic acid (1.23 g, 6.46 mmol) was stirred at 110° C. for 20 h, then allowed to cool. A saturated aqueous NaHCO3 solution (50 mL) was added, and the mixture was extracted with three 30 mL portions of ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated to a brown oil. Column chromatography (0→8% EtOAc/hexanes) afforded of 7-bromo-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazole (43; 1.47 g; 89%).

後処理

  1. temperatureto cool
  2. extractionthe mixture was extracted with three 30 mL portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a brown oil

出典と根拠

ORDレコード
ord-fb67c054dff641d6b20006099f1dc5c3
出典データセット
uspto-grants-2008_04
特許番号
US07365211B2

関連ノート

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