Water → Ethyl 4-oxo-1-{[6-(1,3-thiazol-4-yl)pyridin-3-yl]methyl}-1,4-dihydrocinnoline-3-carboxylate

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Reaction Steps

Ethyl 1-[(6-bromopyridin-3-yl)methyl]-4-oxo-1,4-dihydrocinnoline-3-carboxylate (897 mg, 2.31 mmol), 4-(tributylstannanyl)-1,3-thiazole (1.04 g, 2.77 mmol, 1.2 equiv), copper(I)iodide (176 mg, 0.924 mmol, 0.4 equiv), cesium fluoride (702 mg, 4.62 mmol, 2 equiv) and tetrakis(triphenylphosphine)palladium(0) (534 mg, 0.462 mmol, 0.2 equiv) were combined in degassed N,N′-dimethylformamide (6 mL) and stirred for 1 hour at ambient temperature. The mixture was poured into water and extracted twice with ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in chloroform, treated with potassium fluoride on Celite (8 g, 10 weight equiv) and after stirring vigorously for 24 hours, was filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate; then 100:0 to 95:5; chloroform:methanol), providing the titled compound.

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