Triphenylphosphine → 4-(2-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-3-amine

Participants

Reaction Steps

To a solution of 4-nitronaphthol (2) (0.95 g, 5.00 mmol), PPh3 (1.97 g, 7.50 mmol) and 2-(3-aminopyridin-4-yl)ethanol (25) (1.04 g, 7.50 mmol) in THF (20 mL) was added dropwise DIAD (590 μL, 3.75 mmol) at −15° C. The mixture was stirred for 1 hr at RT and the volatiles removed in vacuo. The residues was absorbed on silica (20 g) and purified by column chromatography (SiO2, 80 g, 50-100% EtOAc in isohexane, gradient elution and then 5% MeOH in EtOAc, isocratic elution) to give the title compound (26) (1.36 g, 88%): m/z 310 (M+H)+ (ES+).

Provenance & Evidence