Cesium carbonate → Ethyl 8-chloro-1-[(6'-methyl-2,3'-bipyridin-5-yl)methyl]-4-oxo-1,4-dihydrocinnoline-3-carboxylate

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Reaction Steps

Ethyl 1-[(6-bromopyridin-3-yl)methyl]-8-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate (0.21 g, 0.49 mmol) was combined with (6-methylpyridin-3-yl) boronic acid (0.19 g, 1.2 mmol, 2.5 equiv), copper(I)chloride (48 mg, 0.49 mmol, 1 equiv), cesium carbonate (0.32 g, 0.97 mmol, 2 equiv), palladium(II)acetate (11 mg, 0.049 mmol, 0.1 equiv), and bis(diphenylphosphino)ferrocene (27 mg, 0.049 mmol, 0.1 equiv) in degassed N,N-dimethylformamide (3 mL). The mixture was placed into an oil bath preheated at 95° C. for 15 minutes, cooled to ambient temperature, diluted with water (5 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed once with water and brine, dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Provenance & Evidence