Cl[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.C(O[C:13](=[S:15])[S-:14])C.[K+].CN1C(=O)CCC1.O>C(O)(=O)C>[Cl:9][C:4]1[N:3]=[C:2]2[S:14][C:13]([SH:15])=[N:8][C:7]2=[CH:6][CH:5]=1To a round bottom flask was added 2,6-dichloropyridin-3-amine (21.4 g, 131 mmol), potassium ethoxy(thioxo)methanethiolate (42.1 g, 262 mmol), and anhydrous NMP (300 mL). The reaction mixture was then heated to 170° C. while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 3.5 hours. The crude reaction mixture was then allowed to cool to room temperature, and acidified to pH 5 with glacial acetic acid, which led to a precipitate which was collected by filtration. This precipitate was then suspended in ethyl acetate and washed with water, then brine, dried over sodium sulfate, filtered, and concentrated to give 5-chloro[1,3]thiazolo[5,4-b]pyridine-2-thiol (1-1) as a tan solid. HRMS (M+H)+: observed=202.9502, calculated=202.9499.
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