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

Participants

Reaction Steps

To a solution of 4-nitronaphthol (0.95 g, 5.00 mmol), PPh3 (1.97 g, 7.50 mmol) and 2-(3-aminopyridin-4-yl)ethanol (16) (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 (80 g) gradient elution with 50-100% EtOAc/iso-hexane and final elution with 5% MeOH/EtOAc to give 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-3-amine a yellow solid (17) (1.36 g, 88%): m/z 310 (M+H)+ (ES+).

Provenance & Evidence