Binap, (A+-)- → 5-{1-[2-((S)-1-Phenyl-ethylamino)-pyridin-4-yl]-1H-indazol-3-yl}-(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

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To a solution of [4-(3-chloro-indazol-1-yl)-pyridin-2-yl]-(1-phenyl-ethyl)-amine (0.17 g, 0.48 mmol) in toluene (3 mL) under nitrogen were added palladium acetate (0.011 g, 0.05 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.03 g, 0.05 mmol), and t-butyl(1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.14 g, 0.72 mmol), followed by sodium t-butoxide (0.13 g, 1.3 mmol). The resulting mixture was stirred at 90° C. for 20 h. After cooling to room temperature, the reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate and brine; dried (MgSO4). Flash chromatography of the crude product mixture with 25:10:65, 40:10:50, 50:10:40, 60:10:30, and 70:10:20 EtOAc-CH2Cl2-Hexane gave the title compound. MS (ES+): 511.4 [M+H]+, 509.2 [M−H]−.

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