[Cl:1][C:2]1[C:10](I)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:12]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[C:10]([CH3:12])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1A mixture of the title compound from Example 1 Step A (0.30 g, 1.077 mmol), palladium acetate (0.024 g, 0.108 mmol), methyl boronic acid (0.129 g, 2.155 mmol), cesium carbonate (1.053 g, 3.23 mol) and triphenylphosphine (0.057 g, 0.215 mmol) in tetrahydrofuran (5.39 mL) was heated in a sealed tube at 100° C. for 18 hours. The reaction was then cooled to room temperature, filtered and concentrated under reduced pressure. Purification by column chromatography on silica gel (0-15% ethyl acetate in hexanes) provided the title compound: LCMS m/z 166.94 [M+H]+, 168.89 [M+2+H]+; 1H NMR (500 MHz, CDCl3) 8.30 (d, J=6.9 Hz, 1 H), 7.35 (d, J=8.9 Hz, 1 H), 7.10 (dd, J=7.7, 7.7 Hz, 1 H), 6.70 (dd, J=6.6, 6.6 Hz, 1 H), 2.30 (d, J=1.2 Hz, 3 H).
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