C(N(CC)CC)C.Br[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([S:15][CH3:16])[CH:14]=1.[C:17]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23])#[CH:18]>C(OCC)(=O)C.[Cu]I.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>[CH3:16][S:15][C:13]1[CH:14]=[C:9]([C:18]#[C:17][C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])[CH:10]=[N:11][CH:12]=1Add copper (I) iodide (20.0 mg, 0.18 mmol), bis(triphenylphosphine)palladium (II) dichloride (64.2 m g, 0.092 mmol) and triethylamine (1.03 mL, 7.32 mmol), to a solution of 3-bromo-5-methylsulfanylpyridine, (prepared as described in PREPARATION 29), (375 mg, 1.83 mmol) and 3-ethynylbenzonitrile, (prepared as described in PREPARATION 8), (465 mg, 3.66 mmol) in ethyl acetate (3 mL) and stir at 90° C. overnight. Cool to room temperature, concentrate and purify the residue by silica gel chromatography, eluting with hexanes/ethyl acetate, to give the title compound (187 mg, 41%).
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