Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C(N(CC)CC)C.[C:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)#[CH:17]>C(#N)C.C(OCC)(=O)C.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>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:17]#[C:16][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:7]=1
Heat a suspension of 3,5-dibromopyridine (4.00 g, 16.88 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.59 g, 0.84 mmol) and copper (I) iodide (0.32 g, 1.69 mmol) in triethylamine (4.7 mL, 33.8 mmol) to 80° C. Add a solution of 1-ethynyl-4-fluorobenzene (2.03 g, 16.88 mmol) in acetonitrile (34 mL), stir for 2 h, cool to room temperature and dilute with ethyl acetate. Wash with an aqueous saturated solution of sodium bicarbonate, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with a 1% solution of ethyl acetate in 1:1 chloroform:hexanes, and then recrystallize from methanol to give the title compound (2.4 g, 51.5%).
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