Methyl iodide → 5-Bromo-6-fluoro-1-methyl-1H-indazole

HRID 1892296Notes

Reaction equation

HRID 1892296 reaction equation
[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.[CH3:12]C([O-])(C)C.[K+].CI>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7]([CH3:12])[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 468639235-Bromo-6-fluoro-1H-indazole

Product 1

HCID 579172745-Bromo-6-fluoro-1-methyl-1H-indazoleYield 43.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-6-fluoro-1H-indazole (4 g, 18.60 mmol) in DMF (20 mL) was added potassium 2-methylpropan-2-olate (2.087 g, 18.60 mmol). The resulting mixture was stirred for 40 min. CH3I (3.17 g, 22.32 mmol) was added dropwise. After stirring overnight, the reaction mixture was quenched with NH4Cl (aq), extracted with EtOAc, washed with NH4Cl (aq), dried over Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified with silica gel column chromatography with gradient hexanes:EtOAc to give 5-bromo-6-fluoro-1-methyl-1H-indazole (1.86 g, 42%) as light yellow solid.

Workup

  1. stirringAfter stirring overnight
  2. customthe reaction mixture was quenched with NH4Cl (aq)
  3. extractionextracted with EtOAc
  4. washwashed with NH4Cl (aq)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product, which
  9. customwas purified with silica gel column chromatography with gradient hexanes

Sources & evidence

ORD record
ord-6773249a0def4629bf59bf862b21d5e7
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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