Pyrazole → HCID 57813693, compound

HRID 332845Notes

Reaction equation

HRID 332845 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-ce3b4e0decf14abb8cbfd51bc55f21e1
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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