(S)-tert-Butyl 3-amino-2-oxo-1,4′-bipiperidine-1′-carboxylate (Example 39, Steps A-C, 5.0 g, 17 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.0 g, 1.7 mmol), 1-bromo-2-fluoro-4-(methylsulfonyl)benzene (6.4 g, 25 mmol) and NaOtBu (1.9 g, 20 mmol) were dissolved in degassed toluene (100 mL). Pd2 dba3 (0.77 g, 0.84 mmol) was added and the reaction heated in an 80° C. oil bath for 5 hours. The reaction was concentrated and purified over silica gel (50-100% EtOAc in hexanes followed by 5% ammoniated methanol in CH2Cl2) to afford tert-butyl 3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxo-1,4′-bipiperidine-1′-carboxylate (8.4 g, 18 mmol, 106% yield) as yellow solid.
