[Br:1][C:2]1[C:3]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2I)=[N:4][CH:5]=[CH:6][CH:7]=1>C(NCC)C.CCOCC.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>[Br:1][C:2]1[C:3]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[C:7]#[C:2][CH2:3][CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=13-Bromo-2-(5-chloro-2-iodo-phenoxymethyl)-pyridine (3.8 g, 8.9 mmol), is placed in a pressure flask, dissolved in diethylamine:acetonitrile:THF (18 mL:4 mL:4 mL), and degassed with nitrogen for 15 min. An excess of 1-butyne is bubbled through the solution followed by the addition of Cut (507 mg, 2.66 mmol), and PdCl2(PPh3)2 (623 mg, 0.888 mmol). The mixture is stirred at room temperature for 1 h. The mixture is then diluted with ether and washed with saturated aqueous ammonium chloride and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The residue is purified by flash chromatography (Biotage® Si65M, 30% hexane/CH2Cl2 then 20% ethyl acetate/hexane) to provide 2.3 g (75%) of the title compound as a pale orange solid. LCMS m/e 351 [M]+.
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