Potassium Carbonate → HCID 117736833, compound

Participants

Reaction Steps

A microwave vial was charged with 1-(5,6-dichloro-2-methoxypyridin-3-yl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.100 g, 0.214 mmol), (3-fluorophenyl)boronic acid (0.045 g, 0.321 mmol), potassium carbonate (0.089 g, 0.642 mmol), and Pd(Ph3P)4 (0.025 g, 0.021 mmol). The vial was flushed with Ar (g), then dioxane (0.803 ml) and water (0.268 ml) were added. The reaction was microwaved at 90° C. for 30 minutes. The organic layer was pipetted off of the aqueous layer and concentrated. The resulting film was dissolved in DMSO and filtered through a syringe filter. The resulting solution was purified via reverse phase HPLC (Xbridge 19×100 mm, 10 um, 40 ml/min, 25-85% 0.1% TFA in Acetonitrile) to afford 1-(5-chloro-6-(3-fluorophenyl)-2-methoxypyridin-3-yl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.047 g, 0.089 mmol, 41.7% yield) as a tan solid. 1H NMR (500 MHz, DMSO-d6) δ=11.67 (br. s., 1 H), 8.73 (d, J=1.6 Hz, 1 H), 8.40 (d, J=1.9 Hz, 1 H), 8.30 (s, 1 H), 8.27 (d, J=9.7 Hz, 1 H), 7.87 (dd, J=2.1, 9.0 Hz, 1 H), 7.73 (d, J=7.7 Hz, 1 H), 7.67 (d, J=9.7 Hz, 1 H), 7.64-7.58 (m, 1 H), 7.42-7.33 (m, 1 H), 7.04 (d, J=9.0 Hz, 1 H), 6.84 (d, J=9.7 Hz, 1 H), 6.46 (d, J=1.6 Hz, 1H), 3.83 (s, 3H). m/z (ESI) 527.1 (M+H)+.

Provenance & Evidence