Methyl iodide → 3-iodo-1-methyl-5-(trifluoromethyl)-1H-indazole

HRID 246635Notes

Reaction equation

HRID 246635 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[NH:4][N:3]=1.[CH3:15]C([O-])(C)C.[K+].IC>C1COCC1>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:13])([F:12])[F:14])[CH:9]=2)[N:4]([CH3:15])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178506093HCID 178506093, compound

Product 1

HCID 712801053-iodo-1-methyl-5-(trifluoromethyl)-1H-indazoleYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-iodo-5-(trifluoromethyl)-1H-indazole (4.0 g, 12.8 mmol) in THF (80 mL) was added t-BuOK (2.0 g, 17.9 mmol) slowly at 0° C. and mixture stirred for 30 minutes, iodomethane (1.1 mL, 17.9 mmol) was added at 0° C., then warmed to room temperature and stirred for 1.5 hours, quenched with water (30 mL) and extracted with EtOAc (3×30 mL), the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was washed with ether (5 mL) and filtered to give 3-iodo-1-methyl-5-(trifluoromethyl)-1H-indazole (3.3 g, 79.3%) as a white solid. LCMS: (M+H)+=327.

Workup

  1. stirringstirred for 1.5 hours
  2. customquenched with water (30 mL)
  3. extractionextracted with EtOAc (3×30 mL)
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. washThe crude product was washed with ether (5 mL)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b169146a8fef4a42839ed2f594085684
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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