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.[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][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:30][C:3]1[C:2]([C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([F:31])[CH:37]=2)=[CH:7][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])=[C:5]([O:28][CH3:29])[CH:4]=1
Reactant: OB(O)c1cccc(F)c1
Reactant: COc1cc(Cl)c(Br)cc1-n1c(=O)ccc2cc(S(=O)(=O)Nc3ccon3)ccc21
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(-c2cccc(F)c2)cc1-n1c(=O)ccc2cc(S(=O)(=O)Nc3ccon3)ccc21
Temperature: 90 °C
Yield: 25.5 %

Procedure:
1-(5-Bromo-4-chloro-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.096 g, 0.188 mmol), (3-fluorophenyl)boronic acid (0.039 g, 0.282 mmol), potassium carbonate (0.078 g, 0.564 mmol), and Pd(PPh3)4 (0.022 g, 0.019 mmol) were combined in 1,4-dioxane (0.705 ml) and water (0.235 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 through a Radley's phase separator, and concentrated in vacuo. The crude material was purified via MPLC, eluting with 0-100% ethyl acetate in heptanes, to yield 1-(6-chloro-3′-fluoro-4-methoxy-[1,1′-biphenyl]-3-yl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.025 g, 0.048 mmol, 25.3% yield) as a white solid. m/z (ESI) 526.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.76 (s, 3 H) 6.44 (d, J=1.76 Hz, 1 H) 6.80 (d, J=9.54 Hz, 1 H) 6.93 (d, J=9.12 Hz, 1 H) 7.21-7.36 (m, 3 H) 7.54 (d, J=12.96 Hz, 2 H) 7.85 (dd, J=8.97, 2.13 Hz, 1H) 8.22 (d, J=9.64 Hz, 1 H) 8.36 (d, J=1.97 Hz, 1 H) 8.72 (s, 1 H) 11.49-11.64 (m, 1 H) 11.67 (s, 1 H). 1-(6-chloro-3′-fluoro-4-methoxy-[1,1′-biphenyl]-3-yl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide was separated by chiral SFC on a (S,S) Whelk-O column, eluting with 40% methanol to yield (P)-1-(6-chloro-3′-fluoro-4-methoxy-3-biphenylyl)-N-3-isoxazolyl-2-oxo-1,2-dihydro-6-quinolinesulfonamide as peak 1 and (M)-1-(6-chloro-3′-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) 526.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.75 (s, 3 H) 6.14 (d, J=0.93 Hz, 1 H) 6.69 (d, J=9.64 Hz, 1 H) 6.73 (d, J=8.81 Hz, 1 H) 7.18-7.26 (m, 1 H) 7.29-7.34 (m, 2 H) 7.43-7.55 (m, 3 H) 7.74 (dd, J=8.81, 1.97 Hz, 1 H) 8.09-8.29 (m, 4 H). Data for peak 2: m/z (ESI) 526.0 (M+H)+. 1 H NMR (400 MHz, DMSO-d6) δ ppm 3.75 (s, 3 H) 6.08-6.15 (m, 1 H) 6.68 (d, J=9.64 Hz, 1H) 6.72 (d, J=8.71 Hz, 1 H) 7.16-7.26 (m, 1 H) 7.27-7.35 (m, 2 H) 7.41-7.55 (m, 3 H) 7.73 (dd, J=8.71, 1.97 Hz, 1 H) 8.08-8.25 (m, 4 H).