Sodium Hydroxide → HCID 84727903, compound

HRID 1497358Notes

Reaction equation

HRID 1497358 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.[CH2:17]([O+](CC)CC)[CH3:18].[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]([CH2:17][CH3:18])[N:7]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723982Triethyloxonium tetrafluoroborateHCID 178434225HCID 178434225, compound

Product 1

HCID 84727903HCID 84727903, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-3-methyl-1H-indazole (8.44 g) in ethyl acetate (100 ml) was added dropwise triethyloxonium tetrafluoroborate (1 M dichloromethane solution, 60 ml) at room temperature, and the mixture was stirred at the same temperature overnight. To the reaction mixture was added a 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. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (1.3 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-165416b5939f40028c1703667155e057
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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