2-Chloro-4-(trifluoromethyl)pyridine → (1S,4S)-tert-butyl 5-(4-(trifluoromethyl)pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

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A 2.0-5.0 mL microwave vial was charged with (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (150 mg, 0.76 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (47.1 mg, 0.08 mmol), Sodium tert-butoxide (87 mg, 0.91 mmol), 2-Chloro-4-(trifluoromethyl)pyridine (0.117 mL, 0.91 mmol) and and mixture of toluene (2.5 mL) and DMF (.5 mL). The reaction mixture was degassed for 10 minutes with nitrogen, and then Tris(dibenzylideneacetone)dipalladium(0) (34.6 mg, 0.04 mmol) was added. The reaction mixture was stirred at 120°C under microwave irradiation for 30 minutes. The solution was then irradiated for another 30 min at 120°C. The solution was diluted with EtOAc and washed with saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was loaded on a 24g silica gel column and purified on a Teledyne Isco instrument, eluting with 10% to 40% ethyl acetate in heptane to provide (1S,4S)-tert-butyl 5-(4-(trifluoromethyl)pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (88 mg, 33.9 %) as a solid. MS m/z 344.2 [M+H]+ (ESI)

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