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

HRID 902554Notes

Reaction equation

HRID 902554 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-fb67c054dff641d6b20006099f1dc5c3
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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