[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[O-].[Na+]>CO.[OH-].[Na+].[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1A mixture of 3.4 g (14.3 mmol) of 2-chloro-5 iodopyridine, 1.9 g (17.2 mmol) of thiophenol, 0.93 g (17.2 mmol) of sodium methoxide and 0.36 g (5.7 mmol) of copper in 18 mL of MeOH is heated for 12 hours at 80° C. After cooling to room temperature, the medium is taken up in 100 mL of 1N NaOH and the MeOH is evaporated off under reduced pressure. The reaction medium is extracted with EtOAc (2×100 mL), the organic phase is washed with 0.1N NaOH (2×30 mL), and then dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc mixture (8/2). 1.90 g of 2-chloro-5-(phenylsulfanyl)pyridine are obtained in the form of a white powder.
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