Potassium Carbonate → Perfluorophenyl 1-(3'-chloro-2,5'-difluoro-5-methoxy-[1,1'-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

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Reaction Conditions

Reaction Steps

A RBF was charged with perfluorophenyl 1-(4-bromo-5-fluoro-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate, (3-chloro-5-fluorophenyl)boronic acid (1.310 g, 7.52 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.307 g, 0.376 mmol), and potassium carbonate (2.60 g, 18.79 mmol). The flask was flushed with Ar (g), then 1,4-dioxane (14.09 ml) and water (4.70 ml) were added. A reflux condenser was attached, and the flask was heated for 50° C. for 1.5 h. The mixture was cooled, diluted with water, and extracted with EtOAc (3×). The combined organic extracts were concentrated. The residue was purified by chromatography on silica gel (80-g Redi-Sep Gold column, 25-g silica gel loading column, 0-50% EtOAc/Heptane). Several mixed fractions were discarded, and the resulting fractions containing product were combined and concentrated to give a tan solid. The solid was concentrated from DCM, then taken up in DCM and filtered. The filtrate was concentrated to give perfluorophenyl 1-(3′-chloro-2,5′-difluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (1.646 g, 2.56 mmol, 68.0% yield) as a tan solid. 1 H NMR (400 MHz, DMSO-d6) □=8.62 (d, J=2.3 Hz, 1 H), 8.28 (d, J=9.6 Hz, 1 H), 8.00 (dd, J=2.3, 9.1 Hz, 1 H), 7.72-7.57 (m, 4H), 7.52 (d, J=6.8 Hz, 1 H), 6.93 (dd, J=9.4, 10.4 Hz, 2 H), 3.78 (s, 3 H).

Provenance & Evidence