Cl[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B1OC(C)(C)C(C)(C)O1.C1C2CC3(N)CC(C2)CC1C3.Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+3].C([O-])(=O)C.C([O-])(=O)C.C(Cl)Cl.O.O1CCOCC1>[F:10][C:8]1[CH:7]=[CH:6][C:3]2[C:2]([CH:9]=1)=[C:13]1[C:12]([CH:17]=[CH:16][CH:15]=[CH:14]1)=[N:11][C:4]=2[NH2:5]To a solution of 2-chloro-4-fluorobenzonitrile (1.0 g, 6.42 mmol), 2-aminophenylboronic acid pinacol ester (1.6 g, 7.1 mmol), palladium(III) acetate (0.07 g, 0.32 mmol), amantadine hydrochloride (0.24 g, 1.3 mmol) and cesium carbonate (4.6 g, 14.1 mmol) were added to dioxane previously deaerated with nitrogen and heated to reflux for 17 hours. After cooling, both distilled water and methylene chloride (50 mL) were added to the reaction mixture. The solvent layer was separated and concentrated to give a crude oil that was purified by column chromatography by first using 1:1 ethyl acetate and hexanes ratio followed by 4:1 ethyl acetate/hexanes as the eluants. The pure product was collected to give 9-fluoro-6-phenanthridinamine (42 g, 32% Yield) whose NMR spectrum is consistent with the proposed structure.
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