Water → N-Benzyl-N',N'-dimethyl-N-[3-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-propane-1,3-diamine

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Reaction Conditions

Reaction Steps

A mixture of 5-bromo-1-trityl-1H-benzotriazole (220 mg, 0.5 mmol), N-benzyl-N-(3-boranyl-benzyl)-N′,N′-dimethyl-propane-1,3-diamine (180 g, 0.55 mmol), and cesium carbonate solution in water (2M, 1 mL, 2 mmol) taken altogether in 10 mL of dioxane was degassed (evacuate in vacuo and pressurize with argon, two times) and PdCl2(dppf).DCM (21 mg, 0.025 mmol) was added and the mixture was degassed two more times as described above. The resulting mixture was heated at 90° C. for 3 h, then it was allowed to cool to room temperature and the volatiles were removed in vacuo. The residue was partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane and the combined organic phases were dried over MgSO4, filtered and evaporated to give the crude product. Chromatography on silica gel (elution with methanol/dichloromethane) followed by trituration of the material obtained with diethyl ether gave 68 mg of the title compound.

Provenance & Evidence