[C:1]([NH:4][NH:5][C:6](=[S:15])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[Br:14])(=O)[CH3:2].Cl>C(=O)([O-])O.[Na+]>[Br:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[N:7]1[C:1]([CH3:2])=[N:4][N:5]=[C:6]1[SH:15]2-acetyl-N-(3-bromopyridin-4-yl)hydrazinecarbothioamide (200 mg, 0.6917 mmol) was dissolved in sodium hydrogen carbonate (4 mL,) and stirred at 50° C. for 2 hrs and at 100° C. for 5 hrs. The reaction mixture was then allowed to stand at RT for 48 h before it was carefully neutralised with dilute HCl and partitioned with 10% MeOH in DCM. The aqueous layer was extracted with further 10% MeOH in DCM (3×10 mL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give 4-(3-bromopyridin-4-yl)-5-methyl-4H-1,2,4-triazole-3-thiol as an orange solid (152.6 mg). MS (ES+) 272.9.
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