Pyrazole → [3-(1H-Pyrazol-1-yl)phenyl]acetic acid

HRID 1179537Notes

Reaction equation

HRID 1179537 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[C:6]([O-:9])([O-])=[O:7].[Cs+].[Cs+].[C@@H]1(N)CCCC[C@H]1N.CCCCC[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[OH-].[Na+]>O1CCOCC1.[Cu]I>[N:1]1([C:30]2[CH:31]=[C:26]([CH2:25][C:6]([OH:9])=[O:7])[CH:27]=[CH:28][CH:29]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

8

Reactant 5

HCID 1048PyrazoleHCID 8182DodecaneHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 438061,2-Diaminocyclohexane, trans-

Product 1

HCID 21062671[3-(1H-Pyrazol-1-yl)phenyl]acetic acidYield 65%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

Pyrazole (1.2 eq), Cs2CO3 (2.5 eq), CuI (0.5 eq), trans-1,2-cyclohexanediamine (0.6 eq) and dodecane (1 eq), were added to a stirred solution of 3-bromophenylacetic add (1 eq) in dioxane at room temperature under an inert atmosphere. The mixture was irradiated in a microwave reactor (PersonalChemistry Emrys™ Optimiser, 300W, 160° C., 20 min), then added to a 1N aqueous solution of NaOH, and extracted with Et2O. The aqueous phase was acidified to pH=3 with HCl 2N, then extracted with ethyl acetate; this phase was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (Silica) eluting with a gradient from Cyclohexane/ethyl acetate 8:2, to Cyclohexane/ethyl acetate 1:1, affording the title compound in 65% yield.

Workup

  1. extractionextracted with Et2O
  2. extractionextracted with ethyl acetate
  3. washthis phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customThe crude material was purified on SPE cartridge (Silica)
  7. washeluting with a gradient from Cyclohexane/ethyl acetate 8:2, to Cyclohexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-bc919c8883a84953abab0f1dc955e1b3
Source dataset
uspto-grants-2007_10
Patent number
US07279481B2

Reaction notes

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