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

HRID 902554

반응식

HRID 902554 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-fb67c054dff641d6b20006099f1dc5c3
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365211B2

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