Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → 4-Bromo-2-methyl-2H-indazole

HRID 1639763Notes

Reaction equation

HRID 1639763 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.F[B-](F)(F)F.[CH3:16][O+](C)C>C(OCC)(=O)C>[Br:1][C:2]1[C:3]2[C:7]([CH:8]=[CH:9][CH:10]=1)=[N:6][N:5]([CH3:16])[CH:4]=2

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 223525484-bromo-1H-indazole

Product 1

HCID 225590314-Bromo-2-methyl-2H-indazoleYield 95.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-bromo-1H-indazole (2.24 g, 11.4 mmol) in ethyl acetate (110 mL) was added trimethyloxonium tetrafluoroborate (2.19 g, 14.8 mmol) at room temperature, and the mixture was stirred for 3 hr. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (2.29 g, yield 95%).

Workup

  1. washwashed with aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-c01811fb97ed44e7b82c931aae8cf18b
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

Loading…