Potassium Carbonate → methyl N-[[2-chloro-5-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl N-[[(2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (prepared according to a procedure described in World Patent Publication WO 2008/124092) (600 mg, 2.2 mmol) in dioxane (60 mL) was added trans-N,N′-dimethylcyclohexane-1,2-diamine (60 mg, 0.452 mmol) under nitrogen atmosphere. Then copper(I) iodide (86 mg, 0.452 mmol) and potassium carbonate (1.87 g, 13.5 mmol) were added to form a dark-green-colored reaction mixture. To the reaction mixture was added 3,4-dihydro-6-iodo-2H-1-benzopyran (882 mg, 3.39 mmol). The reaction mixture was heated at 95° C. under nitrogen overnight, the solvent was evaporated, and the residue was purified by silica gel column chromatography (30% ethyl acetate/petroleum ether as eluant) to provide the title product, a compound of the present invention, as solid (0.318 g).

Provenance & Evidence