tert-Butanol → (8-Bromo-[1,6]naphthyridin-2-yl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

8-Bromo-[1,6]naphthyridine-2-carboxylic acid (1 equiv.) is suspended in tert-butanol (20 mL). Triethylamine (1.1 equiv.) and diphenylphosphoryl azide (1.1 equiv.) are added and the reaction is warmed to reflux. After refluxing for 2.5 hours, the reaction is allowed to cool and half the solvent is removed by rotary evaporation. The residue is dissolved in ethyl acetate (200 mL) and washed with saturated NaHCO3 (50 mL). The organic phase is dried over magnesium sulfate, filtered and concentrated to afford the crude product. Silica gel chromatography (1:1 EtOAc:hexanes) affords the desired BOC amine as a solid, LC/MS (M+H) 324.1.

Provenance & Evidence