C(ON=O)(C)(C)C.[I:8]I.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[CH:19][C:20](N)=[N:21][CH:22]=2)=[CH:13][CH:12]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[N:21][C:20]([I:8])=[CH:19][N:18]=2)=[CH:13][CH:12]=1With the exclusion of light, 4.9 mL (40.0 mmol) tert-butylnitrite and 7.6 g (30 mmol) iodine are added to a solution of 4.8 g (23.3 mmol) 5-(4-chloro-phenyl)-pyrazin-2-ylamine in 100 mL CCl4 and 50 mL DCM and the reaction mixture is stirred overnight at RT. It is combined with 100 mL water and 50 mL 10% Na2S2O3 solution, the organic phase is separated off, washed again with 50 mL 10% Na2S2O3 solution and twice with 50 mL water and dried over MgSO4. It is filtered through activated charcoal, evaporated down i.vac. and the residue is purified by chromatography (silica gel, gradient: PE to PE/EtOAc 8:2).
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