Sodium Carbonate → Ethyl 2-(4-hydroxy-1-methyl-2-oxo-6-phenyl-1,2-dihydroquinoline-3-carboxamido)acetate

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Reaction Steps

A solution of ethyl 2-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (200 mg, 465 μmol), phenylboronic acid (85 mg, 697 μmol), 2M Sodium carbonate (0.7 ml, 1395 μmol), Tetrakis(triphenylphosphine)palladium(0) (5 mg, 5 μmol) and N,N-Dimethylformamide (10 ml) was stirred at 100° C. After 8 hrs, an additional equivalent of the phenyl boronic acid was added, and the mixture was stirred for 15 hrs. The reaction mixture was concentrated on a roto-evaporator and extracted with EtOAc. This product was then washed with water and brine, then dried with MgSO4 and concentrated on a roto-evaporator to give the crude product as a red-orange oil. The crude product was purified by silica flash chromatography (10-75% EtOAc:Hex step gradient) to give the desired product as a white solid. Yield=120 mg. In some cases, ester hydrolysis was observed and the carboxylic acid was isolated.

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