Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → methyl 5-bromo-6-chloro-2-methyl-2H-indazole-4-carboxylate

HRID 887790Notes

Reaction equation

HRID 887790 reaction equation
[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]2[NH:7][N:6]=[CH:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13].F[B-](F)(F)F.[CH3:21][O+](C)C>C(OCC)(=O)C>[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:21])[N:7]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 59145856Methyl 5-bromo-6-chloro-1H-indazole-4-carboxylate

Product 1

HCID 59145870methyl 5-bromo-6-chloro-2-methyl-2H-indazole-4-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of methyl 5-bromo-6-chloro-1H-indazole-4-carboxylate (390 mg, 1.35 mmol) in ethyl acetate (27 mL) was added trimethyloxonium tetrafluoroborate (260 mg, 1.76 mmol) at room temperature, and the mixture was stirred for 2 hr. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60) to give the title compound (336 mg, yield 82%).

Workup

  1. washwashed with saturated 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 (NH, ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-2eebc61cd27f4bcf8fa5c9cf49877192
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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