FC1C=CC=C(F)C=1C(NC1C=CC(C2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[S:16]C=2C)=CC=1)=O.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1.CCO>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:15](=[S:16])[NH2:14]The solution of 2 (0.5 g, 1.73 mmol) in THF (100 mL) with phenyltrimethylammonium tribromide (0.68 g, 1.8 mmol) was heated at 60° C. for 2 hr. Then the solution was quenched with water and extracted with EtOAc (3×50 mL). The combined EtOAc solution was concentrated to give the crude product, which could be used directly for the next step without further purification. The solution of resulting crude product with pyridine-2-carbothioamide (0.24 g, 1.74 mmol) in EtOH was heated at 70° C. overnight. The solution was diluted with water and extracted with EtOAc. Column chromatography (Hexanes/EtOAc=1/1) afforded compound 2 in 51% overall yield.
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