Potassium Phosphate, Tribasic → HCID 117737083, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with (3-(trifluoromethyl)phenyl)boronic acid (188 mg, 0.991 mmol), S-Phos Precatalyst (25.1 mg, 0.033 mmol), and potassium phosphate (281 mg, 1.322 mmol). The vial was flushed with Ar (g), then a solution of 1-(4-chlorophenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (166 mg, 0.330 mmol) in 1,4-dioxane (1322 μl) was added. Water (330 μl) was then added, and the vial was sealed and heated to 120° C. for 30 min in a Biotage Initiator microwave reactor. The mixture was extracted with EtOAc (3×). The combined organic extracts were concentrated. The residue was taken up in MeOH and filtered through a 0.2 micron filter. The resulting solution was purified by reverse-phase HPLC (25-70% CH3CN/H2O with 0.1% TFA). Fractions containing product were combined and lyophilized to give N-3-isoxazolyl-2-oxo-1-(3′-(trifluoromethyl)-4-biphenylyl)-1,2-dihydro-6-quinolinesulfonamide (32.5 mg, 0.064 mmol, 19.23% yield) as an off-white powder. NMR (400 MHz, DMSO-d6) δ=11.62 (s, 1H), 8.69 (d, J=1.9 Hz, 1H), 8.35 (d, J=2.3 Hz, 1H), 8.21 (d, J=9.5 Hz, 1H), 8.10-8.01 (m, 2H), 7.99-7.94 (m, 2H), 7.83-7.70 (m, 3H), 7.52-7.41 (m, 2H), 6.78 (t, J=9.0 Hz, 2H), 6.40 (d, J=1.9 Hz, 1H). m/z (ESI) 511.9 (M+H)+.

Provenance & Evidence