Br[C:2]1[CH:3]=[C:4]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Cs+].[Cs+].[C:28]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][CH:33]=1)(=[O:30])[CH3:29]>CN1C(=O)CCC1.O>[C:14]([C:8]1([C:4]2[CH:3]=[C:2]([S:38][C:35]3[CH:34]=[CH:33][C:32]([NH:31][C:28](=[O:30])[CH3:29])=[CH:37][CH:36]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:15]
4-(3-Bromo-phenyl)-tetrahydro-pyran-4-carbonitrile (1.33 g) was mixed with Na2CO3 (1.59 g), Cs2CO3 (0.651 g) and 4-acetamidothiophenol (1 g) in N-methyl pyrrolidinone (15 mL). The reaction mixture was heated at 130° C. overnight. After cooling, the mixture was poured into iced water. The product precipitated out as a solid, was collected by suction filtration. The solid was recrystallized from a mixture of EtOAc and hexanes to provide N-{4-[3-(4-Cyano-tetrahydro-pyran-4-yl)-phenyl sulfanyl]-phenyl}acetamide(1.4 g, 80% yield).
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