2-Methoxyaniline → HCID 86343778, compound

Participants

Reaction Conditions

Reaction Steps

(E)-Ethyl 3-(2-iodo-5-(N-(isoxazol-3-yl)sulfamoyl)phenyl)acrylate (0.043 g, 0.096 mmol), xantphos (8.33 mg, 0.014 mmol), Pd2(dba)3 (4.39 mg, 4.80 μmol), and freshly ground potassium phosphate (0.061 g, 0.288 mmol) were added to a 1 dram vial and purged with N2. 1,4-dioxane (0.5 ml) and 2-methoxyaniline (0.022 ml, 0.192 mmol) were added and the mixture was evacuated and backfilled with N2 twice and then stirred at 80° C. for 4 hr. The reaction was then cooled to rt and diluted with 1.5 mL MeOH then heated to 80° C. overnight. The reaction was concentrated to remove MeOH, then diluted with EtOAc and 1N HCl. The aqueous layer was extracted twice with EtOAc, the combined organics were washed with brine, dried over Na2SO4, and concentrated. MPLC purification (12 g Snap, 40% [3:1 EtOAc:EtOH]:heptanes) provided N-(isoxazol-3-yl)-1-(2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (24.8 mg, 0.062 mmol, 65.1% yield) as a light yellow solid. m/z (ESI) 396.0 (M−H)−.

Provenance & Evidence