Potassium Carbonate → 3-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

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3-Nitro-N-(1-phenylethyl)-6-(quinolin-5-yl)pyridin-2-amine. To a solution of 6-chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine (2.24 g, 8.07 mmol) and quinolin-5-ylboronic acid (1.81 g, 10.5 mmol) in DMF (150 mL) was added potassium carbonate (4.46 g, 32.3 mmol) in water (25 mL). The reaction solution was purged with a stream of nitrogen followed by the addition of tetrakis(triphenylphosphine)palladium(0) (932 mg, 0.81 mmol). After heating at 85° C. for 2 h, the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography to afford the title compound (2.36 g, 79% yield). MS (ESI) m/z 371.3 [M+1]+.

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