Nitrogen → HCID 117737203, compound

Participants

Reaction Conditions

Reaction Steps

A blue-green dioxane (2.2 mL) slurry of 1-(4-bromo-5-fluoro-2-methoxyphenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.683 g, 1.11 mmol), 2-hydroxy-4-methylpyridine (1.21 g, 11.1 mmol), cesium carbonate (0.543 g, 1.67 mmol), copper(I) iodide (0.212 g, 1.11 mmol), and trans-N,N′-dimethyl-1,2-cyclohexanediamine (0.18 mL, 1.17 mmol) was sparged with N2 for 45 min in a 40-mL vial. The sealed flask was then heated to 110° C. After stirring for 2 h, the reaction was then quenched with H2O and extracted thrice with EtOAc. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Column chromatography (25 g Snap Ultra column, 0% to 80% [3:1 EtOAc/EtOH]/hept gradient with 10% DCM) followed by additional column chromatography (55 g Interchim C18 PuriFlash column, 0-100% MeCN/H2O with 0.1% NH4OH) afforded 1-(5-fluoro-2-methoxy-4-(4-methyl-2-oxopyridin-1(2H)-yl)phenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (25 mg, 0.039 mmol, 3.5% yield). m/z (ESI) 643.2 (M+H)+.

Provenance & Evidence