[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:20][CH3:21])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)=[O:5])[CH3:2].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:20][CH3:21])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:13][CH:12]=1)=[O:5])[CH3:2]Combine 3-(4-Iodophenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester (50 mg, 0.12 mmol), morpholine (20 μl, 0.23 mmol), Pd2(dba)3 (3.5 mg, 0.006 mmol), cessium carbonate (53 mg, 0.16 mmol) and (+)-BINAP (5.4 mg, 0.009 mmol) in anhydrous toluene (1 ml) and stir at 100° C. for 12 hours. Cool the reaction mixture to room temperature, filtered through celite and washed with ethyl acetate. Evaporate the solvent and purify the residue by column chromatography (silica gel) eluting with ethyl acetate:hexane 1:3 to provide the title compound (22 mg, 49%): 1H NMR (CDCl3, 200 MHz): δ 7.37 (d, 2H, J=8.9); 6.99 (d, 2H, J=8.9); 4.22 (q, 2H, J=7.2); 3.89 (m, 4H); 3.28 (m, 4H); 2.71 (s, 3H); 1.24 (t, 3H, J=7.2).
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