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

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazole (i.e. the product of Step A) (600 mg, 3 mmol) in dioxane (50 mL) under nitrogen atmosphere, was added trans-N,N′-dimethylcyclohexane-1,2-diamine (86 mg, 0.6 mmol), followed by the addition of copper(I) iodide (114 mg, 0.6 mmol) and potassium carbonate (2.48 g, 18 mmol) to form a dark green-colored reaction mixture. To this reaction mixture was added methyl N-[(5-bromo-2-chlorophenyl)methyl]carbamate (1.2 g, 4.5 mmol; prepared according to U.S. Pat. No. 6,313,071), and the reaction mixture was heated at 95° C. under nitrogen overnight. The reaction mixture was then concentrated and purified by silica gel column chromatography using 20% ethyl acetate in petroleum ether as eluant to provide the title product, a compound of the present invention, as a solid (110 mg).

Provenance & Evidence