Boron tribromide → 9-(8-Aza-bicyclo[3.2.1]oct-3-yl)-6-pyridin-3-yl-9H-xanthen-4-ol

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Reaction Steps

To a solution of 3-(5-methoxy-3-pyridin-3-yl-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]octane, 7k (0.3 g, 0.803 mmol) in CH2Cl2 (20 mL) was added dropwise a 1M BBr3 solution in methylene chloride (3.2 mL, 3.2 mmol) at 0° C. The mixture was stirred at rt for 24 h, and quenched with a saturated NaHCO3 solution (20 mL). The organic layer was dried over MgSO4 and concentrated. The crude product was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA) to yield 20 mg (4.1%) of title compound 9-(8-aza-bicyclo[3.2.1]oct-3-yl)-6-pyridin-3-yl-9H-xanthen-4-ol, 8k as a TFA salt. MS m/z (MH+) 385.2.

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