Réaction #157421

Équation de réaction

1-chloro-4-iodobenzene

methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate

trans-N,N′-dimethylcyclohexane-1,2-diamine

potassium carbonate

→

title compound

methyl N-[[2-chloro-5-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]phenyl]methyl]-carbamate

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture heated
2. 2
   Températureat reflux overnight
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   AutreThe resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

Mode opératoire

To a mixture of methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. the product of Step B, Example 4) (0.2 g, 0.75 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (0.043 g, 0.3 mmol), copper(I) iodide (0.03 g, 0.15 mmol) and potassium carbonate (−325 mesh) (0.622 g, 4.5 mmol) in dioxane (4 mL) was added 1-chloro-4-iodobenzene (0.27 g, 1.13 mmol). The reaction mixture heated at reflux overnight and then concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (0.156 g) melting at 151-153° C.

Source