[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6](CCC2C(Cl)=CC=CC=2C(N)=S)[CH:7]=1.[SH2:22].BrC1C=CC(OC)=C(C[CH2:31][C:32]2[C:39](Cl)=[CH:38][CH:37]=[CH:36][C:33]=2[C:34]#[N:35])C=1>C(O)C.C(N(CC)CC)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([S:22][CH2:31][C:32]2[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=2[C:34]2[NH:35][CH2:32][CH2:33][CH2:34][N:35]=2)[CH:7]=19, 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-thiobenzamide. As shown in Scheme 9, hydrogen sulfide gas was bubbled into a solution of 2.75 g (7.8 mmol) of 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-benzonitrile in 20 mL of ethanol and triethylamine (5:4 v/v) for 10 minutes. The solution was then heated to 80° C. in a sealed pressure tube for 5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate twice. The organic extracts were washed with brine, dried (MgSO4), filtered and evaporated to give 3.0 g of crude product which was used directly in the next step.
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