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+].N[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[SH:35].C[N:37]1C(=O)CCC1>>[NH2:37][C:33]1[CH:32]=[CH:31][C:30]([S:35][C:2]2[CH:3]=[C:4]([C:8]3([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=2)=[CH:29][CH:34]=14-(3-Bromo-phenyl)-tetrahydro-pyran-4-carbonitrile (133.4 g), Na2CO3 (363.6 g), Cs2CO3 (223.1 g) and aminothiophenol (62.8 g) were heated in N-methyl pyrrolidinone (2.3 L) at 130° C. for 24 hours. More aminothiophenol (35.6 g) was added and heating was continued for another 8 hours. The mixture was cooled to room temperature, poured onto icewater (6.8 L) and filtered off. The product was suspended in water (2.5 L) filtered again and washed with water (1.5 L). The product was then slurried in EtOH (0.5 L), filtered off and dried at 40° C./20 mbar to yield 4-[3-(4-Amino-phenyl sulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile (134.3 g, 86%).
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