[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2[CH:18]=[CH:17][C:11]3[N:12]=[C:13]([S:15][CH3:16])[S:14][C:10]=3[CH:9]=2)[CH:6]=1.ClC1C=C(C=CC=1)C(OO)=[O:24].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2[CH:18]=[CH:17][C:11]3[N:12]=[C:13]([S:15]([CH3:16])=[O:24])[S:14][C:10]=3[CH:9]=2)[CH:6]=1To a stirred mixture of 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (105 mg, 0.3 mmol) from Step 5 of this Example in CH2Cl2 (15 mL) at 0° C. was added 70-75% 3-chloroperoxybenzoic acid (91 mg, 0.4 mmol). After the mixture was stirred at 0° C. for 2 h, saturated aq NaHCO3 (10 mL) was added. The mixture was stirred for 10 min and the CH2Cl2 layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole (130 mg) as a white foam. The material was used in the next step without further purification. LCMS (ESI) m/z 356 and 358 (M+H)+.
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