HCID 117737112, compound → HCID 117737025, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 1-(4-bromo-5-fluoro-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.100 g, 0.202 mmol) and PdCl2(dppf)-CH2Cl2 (0.017 g, 0.020 mmol). The vial was flushed with Ar (g), then THF (1.012 ml) and neopentylzinc bromide, 0.5 M in THF (1.5 ml, 0.750 mmol) were added. The reaction was heated to 70° C. and stirred for one hour. The reaction was purified via column chromatography (RediSep Gold 40 g, gradient elution 10-75% [3:1 EtOAc/EtOH]:Heptane) to afford 1-(5-fluoro-2-methoxy-4-neopentylphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.024 g, 0.049 mmol, 24.43% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ=11.66 (s, 1 H), 8.72 (d, J=1.8 Hz, 1 H), 8.35 (d, J=2.2 Hz, 1 H), 8.21 (d, J=9.6 Hz, 1 H), 7.85 (dd, J=2.2, 9.0 Hz, 1 H), 7.29 (d, J=9.5 Hz, 1 H), 7.10 (d, J=6.6 Hz, 1 H), 6.77 (t, J=9.8 Hz, 2 H), 6.44 (d, J=1.8 Hz, 1 H), 3.64 (s, 3 H), 2.62 (s, 2 H), 0.99 (s, 9 H). m/z (ESI) 486.2 (M+H)+.

Provenance & Evidence