Oxonium, triethyl-, hexafluorophosphate(1-) (1:1) → methyl 5-bromo-2-ethyl-2H-indazole-4-carboxylate

HRID 1639769Notes

Reaction equation

HRID 1639769 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][N:6]=[CH:5][C:4]=2[C:3]=1[C:11]([O:13][CH3:14])=[O:12].F[P-](F)(F)(F)(F)F.[CH2:22]([O+](CC)CC)[CH3:23]>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:22][CH3:23])[N:7]=2)[C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 167684Oxonium, triethyl-, hexafluorophosphate(1-) (1:1)HCID 59145907Methyl 5-bromo-1H-indazole-4-carboxylate

Product 1

HCID 59334535methyl 5-bromo-2-ethyl-2H-indazole-4-carboxylateYield 91.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of methyl 5-bromo-1H-indazole-4-carboxylate (2.00 g, 7.84 mmol) in ethyl acetate (80 mL) was added triethyloxonium hexafluorophosphate (2.92 g, 11.8 mmol), and the mixture was stirred under nitrogen atmosphere at room temperature for 15 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 sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=5/95→50/50) to give the title compound (2.03 g, yield 91%).

Workup

  1. additionwas added
  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 silica gel column chromatography (NH, ethyl acetate/hexane=5/95→50/50)

Sources & evidence

ORD record
ord-8e04857c7a53444f9c0009e3ecc11411
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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