Pyrazole → HCID 57813693, compound

HRID 2200519Notes

Reaction equation

HRID 2200519 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7](Br)[CH:8]=1)[NH2:5].[NH:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Cu+2].O>[N:10]1([C:2]2[CH:3]=[C:4]([CH:6]=[C:7]([N:10]3[CH:14]=[CH:13][CH:12]=[N:11]3)[CH:8]=2)[NH2:5])[CH:14]=[CH:13][CH:12]=[N:11]1.[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)[CH:8]=1)[NH2:5]

Participants

8

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 2215123,5-Dibromoaniline

Product 2

HCID 57813693HCID 57813693, compoundYield 95%HCID 866856353,5-di(1H-pyrazol-1-yl)aniline

Reagents, catalysts & solvents 3

HCID 165397Cupric acetate monohydrateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

The mixture of 3,5-dibromoaniline (1.16 g, 4.6 mmol), pyrazole (0.47 g, 6.9 mmol), Fe(acac)3 (0.35 g, 1.0 mmol), Cu(OAc)2.H2O (0.18 g, 1.0 mmol) and cesium carbonate (3.00 g, 9.2 mmol) in 20 mL DMF was stirred at 135° C. in a sealed tube for 3 days. The mixture was diluted with EtOAc, stirred vigorously, filtered through celite, concentrated in vacuo, subjected to silica flash column to isolate 3,5-di(1H-pyrazol-1-yl)aniline and 3-bromo-5-(1H-pyrazol-1-yl)aniline (0.52 g).

Workup

  1. stirringstirred vigorously
  2. filtrationfiltered through celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b25183a39824df1a7839405ef702775
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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