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

HRID 1639736Notes

Reaction equation

HRID 1639736 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[N:2]1.F[B-](F)(F)F.[CH3:19][O+](C)C>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:19][N:2]1[CH:3]=[C:4]2[C:9]([CH:8]=[CH:7][CH:6]=[C:5]2[C:10]([O:12][CH3:13])=[O:11])=[N:1]1

Participants

5

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 6623327methyl 1H-indazole-4-carboxylate

Product 1

HCID 37818684Methyl 2-methyl-2H-indazole-4-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of methyl 1H-indazole-4-carboxylate (63.0 g, 358 mmol) in ethyl acetate (1.19 L) was added trimethyloxonium tetrafluoroborate (68.8 g, 465 mmol), and the mixture was stirred under nitrogen atmosphere at room temperature for 12 hr. The reaction solution was diluted with ethyl acetate, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by recrystallization (ethyl acetate/hexane) to give the title compound (57.0 g, yield 84%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2bdca5ea3edd4eefb225ab0aef0e997b
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

Loading…