Dimethylformamide → HCID 117737047, compound

Participants

Reaction Steps

A 40-mL vial containing 1-(4-bromo-5-fluoro-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (750 mg, 1.517 mmol) and cesium carbonate (1483 mg, 4.55 mmol) was flushed with N2 and subsequently charged with DMF (2.5 mL) and 4-methoxybenzyl chloride (309 μl, 2.276 mmol). The brown slurry was stirred at rt for 5 d. The reaction was then diluted with H2O and extracted thrice with EtOAc. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to an oily orange residue. Column chromatography (25 g Snap Ultra column, 0% to 100% EtOAc/hept with 10% DCM) afforded 1-(4-bromo-5-fluoro-2-methoxyphenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (697.8 mg, 1.136 mmol, 74.8% yield) as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.71 (d, J=1.76 Hz, 6 H) 4.92 (s, 2 H) 6.74 (s, 1 H) 6.77-6.92 (m, 4 H) 7.22-7.29 (m, 2H) 7.59-7.72 (m, 2H) 7.76 (d, J=9.02 Hz, 1 H) 8.14-8.20 (m, 1 H) 8.38 (d, J=3.45 Hz, 1 H) 8.38 (s, 1 H) 8.82 (d, J=3.25 Hz, 1 H) 8.81 (s, 1 H). m/z (ESI) 614.0 (M+H)+.

Provenance & Evidence