Boron tribromide → 2-(Cyclohexylmethylamino)benzo[d]thiazol-6-ol

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To a solution of N-(cyclohexylmethyl)-6-methoxybenzo[d]thiazol-2-amine (1.40 g, 5.05 mmol) in 12 mL of DCM was added 1 M boron tribromide in DCM (10.6 mL, 10.6 mmol) slowly over about 3 min at 0° C. The reaction solution was stirred at 0° C. for 20 min and at room temperature for additional 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and water (50 mL) and the mixture was stirred at room temperature for 10 min. To the mixture was carefully added excess of solid NaHCO3 until basic and stirring was continued for 1 hour. The mixture was phase separated and the aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed with water (30 mL), saturated NaCl solution (25 mL) and dried over sodium sulfate. This mixture was filter through a plug of silica gel and concentrated under reduced pressure to give the title compound as a solid (1.32 grams). ES/MS m/z 263.1 (MH+).

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