Toluene → N-(5-(4-chloro-3-methylphenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)nicotin-amide

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Reaction Steps

In a 25 ml sealed tube N-(5-bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)nicotinamide (520 mg, 1.38 mmol) was combined with toluene (20 mL). Under argon atmosphere, were added 4-chloro-3-methylphenylboronic acid (471 mg, 2.77 mmol), an aqueous solution of sodium carbonate (2M, 1.38 mL) and Pd(dppf)2Cl2 (30 mg, 0.041 mmol). After two hours at 90° C., the dark re suspension was cooled to room temperature, diluted with ethyl acetate (10 mL), and washed with water (10 mL) and brine (10 mL). The aqueous layer was back-extracted with ethyl acetate (15 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material (760 mg) was purified by flash chromatography (silica gel, 20 g, 20% to 100% ethyl acetate in heptane) to give the title compound as a light brown solid (575 mg, 98%); MS (EI): 422.8 (M+H).

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