Potassium Carbonate → 1-(2-Fluorophenyl)-3-phenyl-1-H-pyrazole

HRID 250757Notes

Reaction equation

HRID 250757 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1I>[Cu](I)I.O1CCOCC1>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:9]1[CH:10]=[CH:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 676731-Fluoro-2-iodobenzeneHCID 178420101HCID 178420101, compound

Product 1

HCID 660139341-(2-Fluorophenyl)-3-phenyl-1-H-pyrazoleYield 36%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Add dioxane (7 mL) to a mixture of 3-phenyl-1H-pyrazole (2 g, 13.9 mmol), copper iodide (132 mg, 0.05 mmol) and potassium carbonate (555 mg, 4.2 mmol). Add 2-fluoroiodobenzene (1.94 mL, 16.6 mmol), trans-cyclohexyldiamine (0.35 mL, 2.78 mmol). Heat at 110° C. for about 18 hours. Cool to RT and filter through a silica gel pad eluting with ethyl acetate. Concentrate and purify (silica gel chromatography, eluting with hexane:ethyl acetate 84:16) to give the desired compound (36%).

Workup

  1. temperatureCool to RT
  2. filtrationfilter through a silica gel pad
  3. washeluting with ethyl acetate
  4. concentrationConcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with hexane:ethyl acetate 84:16)

Sources & evidence

ORD record
ord-338b5c9557c14a3c85715a4dbabb77a4
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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