I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[F:24][C:25]1[C:30](B(O)O)=[CH:29][CH:28]=[CH:27][N:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Pd].O1CCOCC1>[F:24][C:25]1[C:30]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)=[CH:29][CH:28]=[CH:27][N:26]=1A mixture of Intermediate 2 (65 mg, 0.18 mmol) and cesium carbonate (1.5 eq, 88 mg, 0.27 mmol) in a 3:1 mixture of 1,4-dioxan:water (4 ml) was degassed with argon for 5 minutes. Then the mixture was added to (2-fluoro-3-pyridinyl)boronic acid (1.1 eq, 28 mg, 0.20 mmol, Asymchem International Inc.). Palladium acetate (2 mg, 0.01 mmol—alternatively, solid supported palladium may be used), and triphenylphosphine (9 mg, 0.03 mmol) were then added and the whole mixture stirred at reflux for 16 h. The reaction mixture was allowed to cool and partitioned between ethyl acetate (10 ml) and water (10 ml). The organic layer was separated, dried and evaporated. The resulting product was purified using mass directed preparative HPLC to give the title compound (22 mg, 37%).
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