Cl[C:2]1[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:19])[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[BrH:26]>O>[Br:26][C:2]1[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:19])[N:3]=12-Chloro-3-(4-methoxybenzenesulfonyl)-6-methylpyridine (4.74 g, 15.92 mmol) was suspended in HBr (84 mL, 48%). The orange reaction mixture was heated at 110° C. for 24 h. The reaction mixture was cooled to rt, diluted with H2O, and was treated with Na2CO3 until neutral. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to afford a colorless solid (3.22 g, 62% yield) which was used without further purification: mp 99–102° C.; 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=7.7 Hz, 1H), 7.86 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.0 Hz, 1H), 6.95 (d, J=9.1 Hz, 2H), 2.63 (s, 3H); LRMS (APCI) m/z 328.0 [(M+H)+, calcd for C12H11NO3BrS, 328.0].
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