Sodium Hydroxide → 5-bromo-2,3-dimethyl-2H-indazole

HRID 1497356Notes

Reaction equation

HRID 1497356 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH3:11].F[B-](F)(F)F.[CH3:17][O+](C)C.[OH-].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([CH3:11])[N:6]([CH3:17])[N:7]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 178434225HCID 178434225, compound

Product 1

HCID 114995675-bromo-2,3-dimethyl-2H-indazoleYield 80.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-3-methyl-1H-indazole (4.25 g) in ethyl acetate (100 ml) was added trimethyloxonium tetrafluoroborate (4.47 g) at room temperature, and the mixture was stirred at the same temperature for 5 hr. To the obtained reaction mixture was added 1 M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (3.65 g).

Workup

  1. customTo the obtained reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-faf3e695368545d8916b08fb4cf930dd
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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