Under an atmosphere of argon, tert-butyllithium (0.731 mL, 1.24 mmol) was added drop wise over 3 minutes to tetrahydrofuran (5 mL) in a flask cooled in a liquid nitrogen-pentane bath at an external temperature between −105 to −120° C. To the solution was added drop wise over a period of 6 minutes 4-bromo-2-cyclopropylpyridine (123 mg, 0.62 mmol) dissolved in anhydrous tetrahydrofuran (2 mL). The solution was stirred for 4 minutes before drop wise addition of N-((3-bromophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (253 mg, 0.62 mmol) dissolved in anhydrous tetrahydrofuran (2 mL) over a period of 10 minutes. The reaction mixture was stirred at a temperature below −100° C. for 45 minutes. MeOH (5.0 mL) was added at −100° C. and then hydrogen chloride-methanol solution (0.745 mL, 0.93 mmol) was added at −90° C. The reaction was left to stir overnight (17 h) and was allowed to reach ambient temperature. The solvents were evaporated and the residue was partitioned between EtOAc (25 mL) and saturated aqueous NaHCO3 (25 mL). The aqueous layer was extracted with EtOAc (25 mL). The organics were combined, dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography on silica gel and gave 100 mg (38%) of the title compound. MS (ES+) m/z 422, 424 [M+H]+
