[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](Br)[N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1.[C:15]1(C)[CH:20]=CC=C[C:16]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CN(C=O)C.[I-].C([Zn+])CC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:16][CH2:15][CH3:20])[N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1To 128 mg of N-(4-amino-6-bromo-5-cyano-pyridin-2-yl)-acetamide (Example 65A), 6 mg (0.027 mmol) of palladium(II)acetate, and 30 mg (0.098 mmol) of tri(o-tolyl)phosphine was added 0.5 mL of DMF. The mixture was put under N2 and stirred, then 2.0 mL of the n-propylzinc iodide solution was added via syringe. The mixture was heated at 90° C. for 10 minutes then poured into a stirred mixture of 10 mL water and 10 mL ethyl acetate. The metal salts were filtered away through diatomaceous earth, then the layers were separated. The organic layer was extracted with water (2×10 mL), and brine (1×10 mL), dried over MgSO4, filtered, and concentrated to a solid. This was purified via silica gel chromatography, eluting with 50:50 hexanes:ethyl acetate and loading as a solution in hot ethyl acetate to provide 34 mg (31%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.29 (s, 1H), 7.39 (s, 1H), 6.82 (s, 2H), 2.63 (m, 2H), 2.07 (m, 3H), 1.67 (m, 2H), 0.92 (t, 3H, J=7.5 Hz); MS (ESI) m/e 219 (M+H)+; m/e 217 (M−H)−.
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