Reaction SMILES: FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:8]=1[Cl:22])(=O)=O.O.C([O-])([O-])=O.[K+].[K+].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].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:22][C:8]1[CH:9]=[C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:11]=[CH:12][C:7]=1[C:34]1[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=1
Reactant: O=S(=O)(Oc1ccc(-c2nc3ccccc3o2)cc1Cl)C(F)(F)F
Reactant: OB(O)c1cccnc1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: CCCC[N+](CCCC)(CCCC)CCCC
Agent: O=C([O-])[O-]
Solvent: CN(C)C=O
Solvent: O
Product: Clc1cc(-c2nc3ccccc3o2)ccc1-c1cccnc1
Temperature: 75 °C

Procedure:
A suspension of 3-chloro-4-hydroxybenzoic acid (20.0 g, 11.6 mmol) in anhydrous dichloromethane (100 mL) was treated with oxalyl chloride (20 mL, 23.2 mmol) followed by few drops of DMF at 22° C. under argon. After 2 h stirring, the solution became clear, concentrated to dryness, dissolved in dichloromethane (50 mL) and added slowly to a solution of 2-aminophenol (12.6 g, 11.6 mmol) and TEA (9 mL, 11.6 mmol) in anhydrous DMC (50 mL). After 20 min stirring, filtered off salt, concentrated the mixture to afford 4-chloro-3-hydroxy-N-phenylbenzamide as a brown solid. MS (ESI) 264(M+H)+. 4-Chloro-3-hydroxy-N-phenylbenzamide (4 g, 15.2 mmol) was treated with POCl3 (5 mL) at reflux for 1 h. Concentrated and dissolved in dichloromethane (50 mL), washed with sat. NaHCO3 (3×25 mL) and sat. brine (3×25 mL), dried (MgSO4), concentrated in vacuo. The crude residue was chromatographed on silica gel, eluting with 2:1 hexanes:EtOAc to afford 4-(1,3-benzoxazol-2-yl)-2-chlorophenol as a colorless solid. MS (ESI) 246(M+H)+. The solution of 4-(1,3-benzoxazol-2-yl)-2-methoxyphenol (800 mg, 3.3 mmol) in anhydrous DMF (10 mL) was treated with Cs2CO3 (1.1 g, 3.2 mmol) and N-phenyl trifluoromethanesulfonimide (1.2 g, 3.2 mmol) at 22° C. for 30 min. After which time it was quenched with sat. NaHCO3 (20 mL) and diluted with EtOAc (50 mL). The EtOAc solution was washed with sat. brine (3×10 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with 6:1 hexanes:EtOAc to afford 4-(1,3-benzoxazol-2-yl)-2-chlorophenyl trifluoromethanesulfonate a colorless oil. MS (ESI) 378 (M+H)+. The solution of 4-(1,3-benzoxazol-2-yl)-2-chlorophenyl trifluoromethanesulfonate (150 mg, 0.4 mmol) in 6 mL of 2:1 DMF:H2O was degassed via Argon for 10 min. Then K2CO3 (137 mg, 0.99 mmol), Pd(Ph3P)4 (23 mg, 0.02 mmol), n-Bu4NBr (128 mg, 0.40 mmol) and 3-Pyridylboronic acid (73 mg, 0.60 mmol) were added at 22° C. The resulting mixture was then heated at 75° C. for 1 h under Argon. Cooled the reaction mixture to 22° C., then filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to give after purification by flash chromatography (silica gel, 3:1; hexanes:EtOAc) the desired compound, as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.75 (d, 1H), 6.68 (dd, 1H), 8.42 (d, 1H), 8.24 (dd, 1H), 7.89 (dt, 1H), 7.81 (m, 1H), 7.63 (m, 1H), 7.52 (d, 1H), 7.42 (m, 3H). MS (ESI) 307 (M+H)+.