To a degassed solution of tert-butyl 4-(2-hydroxyethyl)naphthalen-1-ylcarbamate (32) (0.64 g, 2.23 mmol) in DMF (10 mL) was added sodium hydride (0.267 g, 60% dispersion in mineral oil, 6.68 mmol) under nitrogen at 0° C. The solution was warmed to RT and was stirred for 30 min and then cooled to 0° C. To this mixture was added a solution of 2-chloro-4-fluoro-pyridine (0.381 g, 2.90 mmol) in DMF (5.0 mL) and the reaction mixture was warmed to RT and stirred for 16 hr. Water was added and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine (3×), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 0-40% ethyl acetate in isohexane, gradient elution) to afford the title compound (33) (0.67 g, 75%); m/z 399 (M+H)+, (ES+).
