[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].C(N(CC)CC)C.[C:18]([C:20]1[CH:21]=[N:22][CH:23]=[C:24]([O:26][CH3:27])[CH:25]=1)#[CH:19]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]#[C:18][C:20]2[CH:21]=[N:22][CH:23]=[C:24]([O:26][CH3:27])[CH:25]=2)=[CH:4][C:3]=1[O:9][CH3:10]
Dissolve 1-fluoro-4-iodo-2-methoxybenzene, (prepared as described in PREPARATION 47), (1.0 g, 4.0 mmol) in triethylamine (15 mL, 108 mmol) and add 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (500 mg, 3.8 mmol) followed by bis(triphenylphosphine)palladium (II) dichloride (100 mg, 0.14 mmol) and copper (I) iodide (60 mg, 0.32 mmol). Stir for 18 h at room temperature, concentrate and purify by silica gel chromatography, eluting with 3:1 hexanes:ethyl acetate. Further purify on silica gel, eluting with 9:1 dichloromethane:ethyl acetate, to give the title compound as a white solid (650 mg, 65%).
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