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

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence