[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O>[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]To a solution of methyl 2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.67 g, 5.30 mmol) in THF (10 mL) was added 2-bromo-3-fluoropyridine (933 mg, 5.30 mmol), tri(o-tolyl)phosphine (67 mg, 0.22 mmol), Na2CO3 (2.25 g, 21.2 mmol) and water (1.6 mL) and the reaction was purged with nitrogen for 15 minutes. Bis(dibenzylidene acetone)palladium (63 mg, 0.11 mmol) was added with further purging with nitrogen for 10 minutes before heating at 80° C. for 1 hour. The reaction was cooled to room temperature and filtered through a pad of arbocel, washing through with EtOAc (50 mL). The filtrate was washed with water (50 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 10-20% EtOAc in heptanes to afford the title compound (240 mg, 21%).
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