Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH:12](N(C(C)C)CC)(C)[CH3:13].C([Sn](CCCC)(CCCC)C=C)CCC>C1(C)C=CC=CC=1.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>[CH:12]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1)=[CH2:13]To a solution of 4-bromo-2-methoxybenzonitrile (−0.5 g, 2.36 mmol, 1.0 eq) in toluene (12 mL) was added diisopropylethylamine (0.61 g, 0.82 mL, 4.72 mmol, 2.0 eq), and tributyl(vinyl)tin (1.12 g, 1.03 mL, 3.54 mmol, 1.5 eq). The reaction mixture was degrassed by bubbling agron through the mixture. Tetrakis(triphenylphosphine)palladium (0.10 g, 0.12 mmol, 0.05 eq) was added and the reaction further degassed before heating to 90° C. for 16 hours. The reaction was cooled and partitioned between EtOAc (100 mL) and NaHCO3 (100 mL). The organics were washed with brine (80 mL), dried (Na2SO4) and concentrated under reduced pressure. MPLC (5→30% EtOAc-hexane) yielded the title compound (0.343 g, 91%) as a white solid; 1H nmr (CDCl3) δ 7.56-7.53 (2H, m, ArH-5, H-6), 6.92 (1H, d, J 9.0 Hz, ArH-2), 6.59 (1H, dd, J 17.5, 11.0 Hz, CH═CH2), 5.63 (1H, d, J 17.5 Hz, CH═CH2 trans), 5.23 (1H, d, J 11.0 Hz, CH═CH2 cis), 3.91 (3H, s, OCH3); m/z 160 [M+H]+.
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