C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]#[CH:16])[CH:14]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]#[C:16][C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[CH:14]=1Sequentially add triethylamine (161 mL, 1156 mmol), bis(triphenylphosphine)palladium(II) dichloride (2 g, 2.89 mmol) and copper (I) iodide (1.1 g, 5.78 mmol) to a solution of 3-bromo-5-ethynylpyridine (52.7 g, 289 mmol), (prepared essentially as described in PREPARATION 23), and 1-fluoro-4-iodobenzene (58.4 g, 262.7 mmol) in acetonitrile (1000 mL). Purge the system with nitrogen and heat the reaction mixture at 50° C. for 16 h. Concentrate, dissolve the residue in 10:1 hexanes:dichloromethane (1000 mL), filter and concentrate. Stir the residue in 150 mL of hexanes at room temperature for 30 min to produce a slurry. Cool the slurry at 0° C. and filter to give the title compound. From the filtrate, a second crop of the title compound can be isolated (45.5 g, 63%).
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