Reaction SMILES: Br[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:20]([NH:23][C:24]4[CH:28]=[CH:27][O:26][N:25]=4)(=[O:22])=[O:21])=[C:16]([F:19])[CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:29])=[C:4]([O:30][CH3:31])[CH:3]=1.[F:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:7]1[CH:6]=[C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:20]([NH:23][C:24]4[CH:28]=[CH:27][O:26][N:25]=4)(=[O:22])=[O:21])=[C:16]([F:19])[CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:29])[C:4]([O:30][CH3:31])=[CH:3][C:2]=1[C:37]1[CH:36]=[CH:35][CH:34]=[C:33]([F:32])[CH:38]=1
Reactant: COc1cc(Br)c(Cl)cc1-n1c(=O)ccc2cc(S(=O)(=O)Nc3ccon3)c(F)cc21
Reactant: OB(O)c1cccc(F)c1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: O=C([O-])[O-]
Agent: [K+]
Product: COc1cc(-c2cccc(F)c2)c(Cl)cc1-n1c(=O)ccc2cc(S(=O)(=O)Nc3ccon3)c(F)cc21
Temperature: 90 °C

Procedure:
A vial was charged with 1-(4-bromo-5-chloro-2-methoxyphenyl)-7-fluoro-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.370 g, 0.700 mmol), (3-fluorophenyl)boronic acid (0.147 g, 1.050 mmol), potassium carbonate (0.290 g, 2.099 mmol), and Pd(Ph3P)4 (0.081 g, 0.88 mmol). The vial was flushed with Ar (g), then 1,4-dioxane (2.62 mL) and water (0.070 mL) were added. The vial was sealed and heated to 90° C. for 30 min. The mixture was cooled and extracted with EtOAc (5×), and the combined organic extracts were concentrated. The residue was purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford racemic 1-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-7-fluoro-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide. 1H NMR (400 MHz, DMSO-d6) δ=12.02 (br. s., 1H), 8.74 (d, J=1.66 Hz, 1H), 8.49 (d, J=7.63 Hz, 1H), 8.26 (d, J=9.59 Hz, 1H), 7.69 (s, 1H), 7.59 (dt, J=6.36, 8.02 Hz, 1H), 7.42-7.48 (m, 2H), 7.29-7.36 (m, 2H), 6.79 (d, J=9.68 Hz, 1H), 6.67 (d, J=12.03 Hz, 1H), 6.40 (d, J=1.76 Hz, 1H), 3.75 (s, 3H). m/z (ESI) 544.1 (M+H)+. This material was purified by chiral SFC on Chiralpak AS-H column (25% MeOH/75% CO2) to give (P)-1-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-7-fluoro-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide as peak 1 and (M)-1-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-7-fluoro-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide as peak 2, both as off-white solids. Data for peak 1: 1H NMR (400 MHz, DMSO-d6) δ=12.02 (br. s., 1H), 8.74 (d, J=1.76 Hz, 1H), 8.49 (d, J=7.77 Hz, 1H), 8.21-8.30 (m, 1H), 7.66-7.71 (m, 1H), 7.54-7.63 (m, 1H), 7.42-7.49 (m, 2H), 7.28-7.37 (m, 2H), 6.79 (d, J=9.64 Hz, 1H), 6.67 (d, J=11.92 Hz, 1H), 6.40 (d, J=1.76 Hz, 1H), 3.75 (s, 3H). m/z (ESI) 544.1 (M+H)+. Data for peak 2: 1H NMR (400 MHz, DMSO-d6) δ=12.02 (br. s., 1H), 8.74 (d, J=1.76 Hz, 1H), 8.49 (d, J=7.77 Hz, 1H), 8.26 (d, J=9.64 Hz, 1H), 7.69 (s, 1H), 7.53-7.63 (m, 1H), 7.42-7.49 (m, 2H), 7.29-7.38 (m, 2H), 6.79 (d, J=9.64 Hz, 1H), 6.67 (d, J=11.92 Hz, 1H), 6.40 (d, J=1.87 Hz, 1H), 3.75 (s, 3H). m/z (ESI) 544.1 (M+H)+.