Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CCO.C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:11][C:10]1[CH:9]=[C:8]2[C:4]([CH:5]=[CH:6][NH:7]2)=[CH:3][C:2]=1[C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1A mixture of 5-bromo-6-fluoro-1H-indole (600.0 mg, 2.80 mmol), 4-methoxyphenyl boronic acid (426.0 mg, 2.80 mmol), 2N aqueous potassium carbonate (8.49 mL, 16.98 mmol) in EtOH (8 mL) and toluene (3 mL) were degassed with N2 for 5 minutes, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (180.0 mg, 0.22 mmol), and degassed for an additional 5 minutes. The reaction mixture was sealed and heated to 80° C. for 16 hours. The reaction was cooled to room temperature and the layers were separated. The organic layer was concentrated in vacuo and the crude material was purified by flash chromatography (25-75% EtOAc/heaptane) to give the title compound (147 mg, 22% yield). MS (ES+) 242.3 (M+1)+.
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