Reaktion #1583827

Reaktionsgleichung

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

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle