Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 59334489, compound

HRID 1639812Notes

Reaction equation

HRID 1639812 reaction equation
[Cl:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.F[B-](F)(F)F.[CH3:20][O+](C)C>C(OCC)(=O)C.O>[Cl:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH3:20])[N:9]=2)[C:5]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 59334582HCID 59334582, compound

Product 1

HCID 59334489HCID 59334489, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 7-chloro-1H-indazole-4-carboxylate (5.40 g, 25.6 mmol) in ethyl acetate (150 mL) was added trimethyloxonium tetrafluoroborate (5.69 g, 38.5 mmol) at room temperature, and the mixture was stirred for 5 hr. The is reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/2) to give the title compound (4.10 g, yield 71%).

Workup

  1. customThe is reaction solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-c480c27de24d4275a9b467f104950681
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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