[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1I.[CH3:13]B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1[CH3:13]A mixture of the title compound from Example 3 Step A (0.500 g, 1.69 mmol), palladium acetate (0.038 g, 0.169 mmol), methyl boronic acid (0.202 g, 3.37 mmol), cesium carbonate (1.65 g, 5.06 mmol) and triphenyl phosphine (0.088 g, 0.337 mmol) in tetrahydrofuran (8.43 mL) was heated in a sealed tube at 100° C. for 18 hours. The mixture was then cooled to room temperature, filtered, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-20% ethyl acetate in hexanes) provided the title compound: LCMS m/z 184.9 [M+H]+ 186.86 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 7.75 (d, J=2.4 Hz, 1H), 7.51 (dd, J=9.7, 4.9 Hz, 1H), 7.14-7.102 (m, 1H), 2.44 (s, 3H).
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