Boron tribromide → HCID 11561890, compound

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Reaction Steps

To a solution of 10-(1-benzyl-piperidin-4-yl)-6-methoxy-10H-phenoxazine-3-carboxylic acid diethylamide, 4d (50 mg, 0.1 mmol) in methylene chloride (2 mL) at 0° C. was added a 1M solution of boron tribromide in methylene chloride (0.8 mL, 0.8 mmol). The mixture was allowed to stir for 15 min at rt, followed by stirring at rt for 4 h. A saturated NaHCO3 solution and methylene chloride were added, and the organic phase was separated. The organic phase was dried, filtered, and evaporated. The residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA) to yield 17 mg (29%) of title compound 10-(1-benzyl-piperidin-4-yl)-6-hydroxy-10H-phenoxazine-3-carboxylic acid diethylamide, 6d as a TFA salt. MS m/z (MH+) 471.0.

Provenance & Evidence