Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][CH2:10]O.C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OBO1.[NH:27]1[CH:31]=C[CH:29]=[N:28]1>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[CH3:29][N:28]1[CH:10]=[C:9]([C:2]2[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=2)[NH2:5])[CH:31]=[N:27]13-Bromoaniline (0.50 mL, 4.6 mmol) was dissolved in 30 mL of PhMe with stirring, and 15 mL of EtOH was added. Na2CO3 (3.06 g, 28.9 mmol) in 15 mL of H2O was added followed by 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-1H-pyrazole (0.955 g, 4.59 mmol). Pd(PPh3)4 (0.265 g, 0.229 mmol) was added, and the mixture was heated to reflux with stirring overnight. The mixture was cooled to rt and poured into EtOAc and H2O. The mixture was filtered through celite, and the layers were separated. The organic layer was washed with brine. The organic layer was concentrated and purified by flash chromatography to afford 0.408 g (51%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 7.92 (s, 1H), 7.65 (s, 1H), 6.96 (t, J=7.7 Hz, 1H), 6.71-6.64 (m, 2H), 6.41-6.36 (m, 1H), 4.99 (br s, 2H), 3.82 (s, 3H).
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