3-Chloro-6-phenylpyridazine → 4-(6-Phenylpyridazin-3-yl)-1,4-diazatricyclo[4.3.1.13,8]undecane

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A solution of the product of Example 2 (0.10 g, 0.66 mmol) in dry toluene (10 mL) was treated with 3-chloro-6-phenylpyridazine (0.20 g, 1.0 mmol; Aldrich), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; 0.01 g, 0.013 mmol; Alfa Aesar), 1,3-bis(2,6-di-iso-propylphenyl)imidazolium chloride (0.017 g, 0.04 mmol; Strem), and sodium tert-butoxide (0.148 g, 1.32 mmol). The mixture was purged with nitrogen and heated to 90° C. for 8 hours. After cooling to room temperature, the reaction was quenched by pouring into a 5% aqueous NaHCO3 solution. The mixture was extracted with chloroform (3×), washed with brine, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography on silica gel, eluting with 2-10% methanol (containing 1% ammonium hydroxide)-chloroform to afford the title compound: MS (DCI/NH3) m/z 307 (M+H)+.

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