Isobutylene oxide → HCID 67416478, compound

HRID 912462Notes

Reaction equation

HRID 912462 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[CH3:20][C:21]1([CH3:24])[CH2:23][O:22]1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:20][C:21]([CH3:24])([OH:22])[CH3:23])=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19]

Participants

6

Reactant 3

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 574187616-Bromo-5-(2,4-difluorophenoxy)-1H-indazole

Product 1

HCID 67416478HCID 67416478, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromo-5-(2,4-difluorophenoxy)-1H-indazole (1.35 g, 4.15 mmol) and 2,2-dimethyloxirane (0.755 mL, 8.30 mmol) in DMA (20 mL) in a sealed tube was added potassium carbonate (1.72 g, 12.5 mmol), and the reaction was heated to 80° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate, and washed twice with water and once with brine. It was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel loaded and eluted with 35% ethyl acetate/hexanes to yield pure 1-(6-bromo-5-(2,4-difluorophenoxy)-1H-indazol-1-yl)-2-methylpropan-2-ol (0.60 g, 36.4% yield).

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed twice with water and once with brine
  3. dry with materialIt was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluted with 35% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ef0391fd30074f4fb3b375e525552942
Source dataset
uspto-grants-2011_09
Patent number
US08026233B2

Reaction notes

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