Potassium Carbonate → HCID 68492755, compound

HRID 1879225Notes

Reaction equation

HRID 1879225 reaction equation
[I:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.Br[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][N:4]2[C:5]([CH3:7])=[CH:6][C:2]([I:1])=[N:3]2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5731534-Fluorophenethyl bromideHCID 145739353-Iodo-5-methyl-1H-pyrazole

Product 1

HCID 68492755HCID 68492755, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 3-iodo-5-methyl-1H-pyrazole (1.45 g, 6.97 mmol) in dimethyl sulfoxide (10 mL) was treated with 1-(2-bromo-ethyl)-4-fluoro-benzene (1.41 g, 6.97 mmol) and potassium carbonate (2.89 g, 20.91 mmol), and the reaction mixture was heated to 95° C. for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), and washed with brine (2×100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (hexanes:ethyl acetate, 1:1) to provide 1-[2-(4-fluoro-phenyl)-ethyl]-3-iodo-5-methyl-1H-pyrazole as a yellow oil. MS (M+H)+=331.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with brine (2×100 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by preparative thin layer chromatography over silica gel (hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-590190abc5ad4c68bec69ba49e62e532
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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