Sodium Hydroxide → 5-Bromo-6-fluoro-1H-indazole

HRID 34128Notes

Reaction equation

HRID 34128 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7](C(=O)C)[N:6]=[CH:5]2.[OH-].[Na+]>C(O)C.Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][N:6]=[CH:5]2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 596944751-(5-bromo-6-fluoro-1H-indazol-1-yl)ethanone

Product 1

HCID 468639235-Bromo-6-fluoro-1H-indazoleYield 88.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 22.5 g of 1-(5-bromo-6-fluoro-indazol-1-yl)ethanone in 250 mL of ethanol was added 20.0 mL of 5N sodium hydroxide aqueous solution at room temperature, and stirred at this temperature for 5 minutes. After neutralizing in 5N hydrochloric acid aqueous solution, the solution was diluted with ethyl acetate. The organic layer was successively washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:3), to afford 16.7 g of the title compound as pale brown crystals.

Workup

  1. washThe organic layer was successively washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-e7a4bb382256414d8ae1d3d86285d24e
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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