Br[C:2]1[C:6]2[CH:7]=[C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[CH3:17][N:18](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][C:13]1[O:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]3[O:4][CH:3]=[C:2]([C:17]#[N:18])[C:6]=3[CH:7]=2)=[N:15][N:14]=1A suspension of 2-(3-bromo-1-benzofuran-5-yl)-5-methyl-1,3,4-oxadiazole (5.58 g, 20.0 mmol), zinc cyanide (1.41 g, 12.0 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.16 g, 1.00 mmol) in N,N-dimethylformamide (50 mL) was stirred at 80° C. for 10 hr under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from hexane/tetrahydrofuran to give the title compound (3.74 g, yield 83%) as colorless crystals.
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