Triphenylphosphine → 2-Amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine

Participants

Reaction Steps

To a solution of 4-nitronaphthol (5.17 g, 27.3 mmol), triphenylphosphine (10.75 g, 41.0 mmol) and 2-aminopyridine-4-methanol (2) (5.09 g, 41.0 mmol) in THF (50 mL), at −15° C., was added dropwise diisopropyl azodicarboxylate (DIAD) (8.07 mL, 41.0 mmol). The mixture was stirred overnight at RT and the volatiles then removed in vacuo. The crude product was triturated from EtOAc (150 mL), filtered off and washed with EtOAc (100 mL). A second trituration from MeOH (100 mL) gave 2-amino-4-[(4-nitronaphthalen-1-yloxy)methyl]pyridine (3) (4.54 g, 56%) as a yellow solid: m/z 296 (M+H)+ (ES+).

Provenance & Evidence