Br[C:2]1[CH:11]=[C:10](Br)[C:9]([NH2:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F-].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[C:14]1([C:2]2[CH:11]=[C:10]([C:2]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:3]=3)[C:9]([NH2:13])=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1According to General Procedure A, a mixture of 5,7-dibromo-8-aminoquinoline (14 g, 100 mg, 0.33 mmol), phenylboronic acid (60 mg, 0.50 mmol), CsF (150 mg, 0.99 mmol), Pd(OAc)2 (1.3 mg, 0.007 mmol) and ligand 12f (5.3 mg, 0.013 mmol) in 1,4-dioxane (2.5 mL) was heated to reflux, cooled and filtered. After evaporation of the solvent, recrystallization from Et2O/hexane gave 51g (86 mg, 88%) as colorless crystals. mp: 100-102° C. (Et2O/hexane). IR (KBr): vmax 3450, 3347, 3050, 3023, 1583 cm−1. 1H NMR (300 MHz, CDCl3): δ 8.85-8.80 (m, 1H), 8.28 (dd, 1H, J=8.4, 1.5 Hz), 7.66-7.63 (m, 2H), 7.54-7.44 (m, 6H), 7.42-7.34 (m, 4H), 5.32 (s, 2H). 13C NMR (75.5 MHz, CDCl3): δ 147.5, 140.2, 139.9, 138.3, 134.2, 130.2, 130.0, 129.2, 129.0, 128.4, 128.2, 127.2, 126.8, 126.1, 121.7, 121.2. EIMS (m/z, (%)): 296 (72), 219 (24), 86 (100), 47 (85). HRMS (EI; m/z): calcd for C21H16N2: 296.1314. Found 296.1312.
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