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

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Reaction Conditions

Reaction Steps

To a solution of N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]formamide (i.e. the product of Step D) (0.25 g, 1.1 mmol) in dioxane (2.5 mL) was added trans-N,N′-dimethylcyclohexane-1,2-diamine (0.06 mL, 0.43 mmol) followed copper(I) iodide (0.08 g, 0.43 mmol), potassium carbonate (0.87 g, 6.4 mmol) and 3,4-dihydro-6-iodo-2H-1-benzopyran (0.45 g, 1.7 mmol; prepared according to the procedure of Muraki et al., Tetrahedron Lett. 1996, 37, 2441). The reaction mixture was heated at 110° C. for 20 h and then cooled to ambient temperature. The solvent was evaporated, and the residue was taken up in chloroform, washed with water and brine, then dried (Na2SO4) and concentrated. The crude residue was then purified by preparative TLC (2% methanol in chloroform as eluant) to provide the title product, a compound of the present invention, as a solid (0.069 g).

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