N,N'-Dimethylethylenediamine → 1-(4-Bromo-phenyl)-3-isopropyl-1H-pyrazole

HRID 625699Notes

Reaction equation

HRID 625699 reaction equation
[CH:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([CH3:3])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CNCCNC>CN(C)C=O.[Cu]I.O>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([N:6]2[CH:7]=[CH:8][C:4]([CH:1]([CH3:3])[CH3:2])=[N:5]2)=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzeneHCID 178439403HCID 178439403, compound

Product 1

HCID 898261621-(4-Bromo-phenyl)-3-isopropyl-1H-pyrazoleYield 95.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-Isopropylpyrazole (588 mg, 5.43 mmol), 1-bromo-4-iodobenzene (15.11 g, 53.4 mmol), cesium carbonate (5.22 g, 16.0 mmol), copper(I)iodide (1.02 g, 5.34 mmol) and N,N′-dimethylethylenediamine (570 uL, 5.34 mmol) are combined in dry N,N-dimethylformamide (100 mL) and heated at 100° C. for 3 hours under a nitrogen atmosphere. The mixture is cooled, poured into water and extracted with diethyl ether. The organic phase is dried and the solvent removed. The residue is purified by flash chromatography (30% dichloromethane in cyclohexane) to give the title compound (Yield 1.37 g) LC (METHOD 5): tR=1.47 min; Mass spectrum (ES+): m/z=265/267 [M+H]+.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with diethyl ether
  3. customThe organic phase is dried
  4. customthe solvent removed
  5. customThe residue is purified by flash chromatography (30% dichloromethane in cyclohexane)

Sources & evidence

ORD record
ord-e30691173bd447abb0e7a5745adab4e3
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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