[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Mg]Br.[Br:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([C:21]2[CH:26]=[CH:25][N:24]=[N:23][CH:22]=2)=[O:20])=[CH:13][CH:12]=1>O1CCCC1.[Cu]I>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:9])[CH2:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[N:23][CH:22]=2)=[O:20])=[CH:13][CH:12]=1To a suspension of copper(I) iodide (63.4 mg, 333 μmol) in tetrahydrofuran (10 ml) was added at 0° C. o-tolylmagnesium bromide solution (2 M in diethyl ether, 3.66 ml, 7.33 mmol) to give a light brown suspension. The reaction mixture was stirred at this temperature for 1½ h, then a solution of (E)-3-(4-bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-one (963 mg, 3.33 mmol) in THF (5.0 ml) was added, then after 1¾ h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; ethyl acetate/heptane 1:1) afforded the title compound (809 mg, 64%). Light yellow foam; MS: 381.1 [M+H]+.
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