[O:1]=[C:2]1[CH2:7][N:6]=[CH:5][C:4]2[CH:8]=[CH:9][S:10][C:3]1=2.CN(C=O)C.[H-].[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1>[Cu](I)I.O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([O:1][C:2]2[C:3]3[S:10][CH:9]=[CH:8][C:4]=3[CH:5]=[N:6][CH:7]=2)=[CH:21][CH:20]=1
Example 145D can be processed as in Lindley (Tetrahedron, 1983, 1433). A solution of Example 145C (1.0 mmol) and DMF (2.0 mL) is treated at 0° C. with sodium hydride (1.0 mmol), slowly warmed to room temperature, treated with 1-chloro-4-iodobenzene (1.0 mmol) and copper iodide (0.1 mmol), heated at 80° C. overnight, and cooled. The solution is poured into water and extracted with diethyl ether. The extracts are combined, dried (MgSO4), filtered, and concentrated. Recrystallization from ethyl acetate/hexanes provides the title compound.
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