Reaction SMILES: Br[C:2]1[C:3]([Cl:30])=[CH:4][C:5]([O:28][CH3:29])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:21][C:22]4[CH:26]=[CH:25][O:24][N:23]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:27])[CH:7]=1.[Cl:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[C:36]([F:38])[CH:37]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.O.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:31][C:32]1[CH:33]=[C:34]([C:2]2[C:3]([Cl:30])=[CH:4][C:5]([O:28][CH3:29])=[C:6]([N:8]3[C:17]4[C:12](=[CH:13][C:14]([S:18]([NH:21][C:22]5[CH:26]=[CH:25][O:24][N:23]=5)(=[O:20])=[O:19])=[CH:15][CH:16]=4)[CH:11]=[CH:10][C:9]3=[O:27])[CH:7]=2)[CH:35]=[C:36]([F:38])[CH:37]=1
Reactant: COc1cc(Cl)c(Br)cc1-n1c(=O)ccc2cc(S(=O)(=O)Nc3ccon3)ccc21
Reactant: OB(O)c1cc(F)cc(Cl)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: [Cl-]
Solvent: O
Solvent: C1COCCO1
Product: COc1cc(Cl)c(-c2cc(F)cc(Cl)c2)cc1-n1c(=O)ccc2cc(S(=O)(=O)Nc3ccon3)ccc21
Temperature: 90 °C
Yield: 64.8 %

Procedure:
1-(5-Bromo-4-chloro-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.484 g, 0.948 mmol), (3-chloro-5-fluorophenyl)boronic acid (0.248 g, 1.421 mmol), potassium carbonate (0.393 g, 2.84 mmol), and Pd(PPh3)4 (0.110 g, 0.095 mmol) were combined in 1,4-dioxane (3.55 ml) and water (1.185 ml). The reaction was heated to 90° C. for 2 h. The reaction was cooled to RT and sat. aq. ammonium chloride was added. The organics were extracted (×3) with DCM, dried via phase separator, and concentrated in vacuo. The crude material was purified via MPLC, eluting with 0-100% ethyl acetate in heptanes, to yield 1-(3′,6-dichloro-5′-fluoro-4-methoxy-[1,1′-biphenyl]-3-yl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.344 g, 0.614 mmol, 64.8% yield). m/z (ESI) 562.0 (M+H)+. 1 H NMR (400 MHz, DMSO-d6) δ ppm 3.76 (s, 3 H) 6.45 (d, J=1.76 Hz, 1 H) 6.79 (d, J=9.64 Hz, 1 H) 6.93 (d, J=9.02 Hz, 1 H) 7.35 (ddd, J=9.59, 2.38, 1.50 Hz, 1 H) 7.39-7.41 (m, 1 H) 7.49 (dt, J=8.73, 2.11 Hz, 1 H) 7.57 (d, J=5.08 Hz, 2H) 7.84 (dd, J=9.02, 2.28 Hz, 1 H) 8.22 (d, J=9.54 Hz, 1 H) 8.37 (d, J=2.18 Hz, 1 H) 8.72 (d, J=1.76 Hz, 1 H) 11.66 (s, 1 H). The material was separated by chiral SFC on a Chiralpak AD with 45% isopropanol to give (P)-1-(3′,6-dichloro-5′-fluoro-4-methoxy-3-biphenylyl)-N-3-isoxazolyl-2-oxo-1,2-dihydro-6-quinolinesulfonamide as peak 1 and (M)-1-(3′,6-dichloro-5′-fluoro-4-methoxy-3-biphenylyl)-N-3-isoxazolyl-2-oxo-1,2-dihydro-6-quinolinesulfonamide as peak 2. Data for peak 1: m/z (ESI) 560.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.76 (s, 3 H) 6.45 (d, J=1.76 Hz, 1 H) 6.79 (d, J=9.64 Hz, 1 H) 6.93 (d, J=8.91 Hz, 1 H) 7.35 (d, J=9.51 Hz, 1 H) 7.40 (s, 1 H) 7.49 (dt, J=8.76, 2.15 Hz, 1 H) 7.57 (d, J=5.18 Hz, 2 H) 7.84 (dd, J=9.02, 2.28 Hz, 1 H) 8.22 (d, J=9.43 Hz, 1 H) 8.37 (d, J=2.28 Hz, 1 H) 8.72 (d, J=1.76 Hz, 1 H) 11.66 (s, 1 H). Data for peak 2: m/z (ESI) 560.0 (M+H)+. 1 H NMR (400 MHz, DMSO-d6) δ ppm 3.76 (s, 3 H) 6.45 (d, J=1.76 Hz, 1 H) 6.79 (d, J=9.64 Hz, 1 H) 6.93 (d, J=8.91 Hz, 1 H) 7.35 (ddd, J=9.61, 2.36, 1.50 Hz, 1 H) 7.39-7.41 (m, 1 H) 7.49 (dt, J=8.71 Hz, 1 H) 7.57 (d, J=5.18 Hz, 2 H) 7.84 (dd, J=8.97, 2.23 Hz, 1 H) 8.22 (d, J=9.54 Hz, 1 H) 8.37 (d, J=2.18 Hz, 1 H) 8.72 (d, J=1.76 Hz, 1 H) 11.66 (s, 1 H).