Pyrazole → HCID 57813693, compound

HRID 1941935Notes

Reaction equation

HRID 1941935 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7](Br)[CH:8]=1)[NH2:5].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[Cs+].[Cs+].[NH:24]1[CH:28]=[CH:27][CH:26]=[N:25]1>CS(C)=O.[Cu]I.O>[Br:1][C:2]1[CH:3]=[C:4]([NH2:5])[CH:6]=[C:7]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)[CH:8]=1

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 145742L-ProlineHCID 2215123,5-Dibromoaniline

Product 1

HCID 57813693HCID 57813693, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3,5-dibromoaniline (0.50 g, 1.99 mmol) in DMSO (2.0 mL) was added sequentially L-Proline (0.041 g, 0.36 mmol), Cs2CO3 (1.16 g, 3.58 mmol), CuI (0.038 g, 0.20 mmol) and pyrazole (0.12 g, 1.80 mmol). The reaction mixture was degassed for 10 min and then heated to 110° C. for 48 h. After the completion of reaction (TLC monitoring), the reaction mixture was cooled to room temperature, added water and extracted with ethyl acetate (×3). The combined organics was washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (230-400 M, 15% EtOAc-Hexane) to get the desired compound (0.18 g, 37%).

Workup

  1. customThe reaction mixture was degassed for 10 min
  2. customAfter the completion of reaction (TLC monitoring)
  3. temperaturethe reaction mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate (×3)
  5. washThe combined organics was washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified over silica gel (230-400 M, 15% EtOAc-Hexane)

Sources & evidence

ORD record
ord-043552292d754f71991237e29e992fbd
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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