Tetrahydrofuran → 3-aminomethyl-2-oxazol-2-yl-1-phenyl-1H-[1, 8]naphthyridin-4-one bis(tert-butyl carbamate)

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one (320 mg, 0.837 mmol), THF (2.79 mL) and DMF (2.79 mL) was added di-tert-butyl iminodicarboxylate (182 mg, 0.837 mmol) and sodium hydride (60% in mineral oil, 33.5 mg, 0.837 mmol). The reaction mixture was heated at 45° C. overnight which turned into a clear yellow solution. The reaction was diluted with a saturated aqueous ammonium chloride solution (30 mL) and was extracted into methylene chloride (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (30%-50% ethyl acetate-hexanes) afforded 3-aminomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one bis(tert-butyl carbamate) (298.7 mg, 68.8%) as an off-white solid.

Provenance & Evidence