[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N:9]2[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]2)[CH:12]=1To a solution of the product from Step 2 (0.477 g, 1.6 mmol) in n-propanol (2.76 mL) and water (0.56 mL) were added 2-chlorophenylboronic acid (0.328 g, 2.1 mmol), palladium acetate (0.001 g, 0.3 mol %), triphenylphosphine (0.004 g, 0.9 mol %) and 2M sodium carbonate (0.96 mL, 1.9 mmol), and the reaction was refluxed for 16 hours. The reaction mixture was cooled and partitioned between EtOAc and water. The organic phase was washed with saturated sodium bicarbonate, brine and dried over sodium sulfate. It was then filtered, concentrated and purified by chromatography using 20% EtOAc in hexanes to yield 0.412 g of the product (79%).
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