Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:9][CH:10]=[CH:11][N:12]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([Sn](C)(C)C)=[CH:16][CH:15]=1.O>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:16][CH:15]=1
A solution of 1.18 g (4.92 mmol) of 1-bromo-2-(thiazol-2-yl)benzene and 1.67 g (6.55 mmol) of 4-metylphenyltrimethylstannane in 20 mL of dimethylformamide was treated with 621 mg of bis(triphenylphosphine)palladium(II) chloride. The reaction mixture was heated at 150° C. for 6 hours, cooled and poured into 300 mL of water. The resultant mixture was extracted with ether (3×100 mL). The combined ether extracts were washed with water (4×), dried over magnesium sulfate and evaporated under vacuum. The residue was purified by chromatography on silica gel, eluting with hexane/ether (100:10) to give 381 mg of the product. EI-MS: calculated for C16H13NS 251; found 250. 1H NMR (200 MHz, CDCl3): 2.36 (s, 3H), 7.14 (s, 4H), 7.24 (d, 1H), 7.40 (m, 1H), 7.42 (m, 2H), 7.73 (d, 1H), 8.20 (dt, 1H).
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