Triphenylphosphine → 1-(4-((1,5-Naphthyridin-2-yl)methoxy)phenyl)-2-(pyridin-4-yl)ethanone

Participants

Reaction Steps

Intermediate 4C, (1,5-naphthyridin-2-yl)methanol (142 mg, 0.887 mmol), Intermediate 4A, 1-(4-hydroxyphenyl)-2-(pyridin-4-yl)ethanone (158 mg, 0.739 mmol), and triphenylphosphine (310 mg, 1.182 mmol) were dissolved in dioxane (6 mL). To this stirred solution was added di-tert-butyl azodicarboxylate (272 mg, 1.182 mmol). The reaction mixture was stirred overnight at ambient temperature under a dry nitrogen atmosphere. The reaction mixture was diluted with aqueous sodium bicarbonate and extracted with CHCl3. The combined organic layers were dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give a yellow oil. The oil was purified by column chromatography on an Analogix IF-280 (Varian SF25-80 g, 100% DCM to 97:3 DCM/2M NH3 in MeOH). Fractions #10-22 were combined and concentrated under reduced pressure to give 1-(4-((1,5-naphthyridin-2-yl)methoxy)phenyl)-2-(pyridin-4-yl)ethanone as a pale green solid (104.5 mg, 39.8%). 1H NMR (300 MHz, CDCl3) δ 9.00 (dd, J=4.2, 1.6 Hz, 1H), 8.55 (dd, J=4.5, 1.6 Hz, 2H), 8.48-8.43 (m, 1H), 8.39 (ddd, J=8.5, 1.6, 0.9 Hz, 1H), 8.01-7.95 (m, 2H), 7.90-7.86 (m, 1H), 7.68 (dd, J=4.5, 1.5 Hz, 2H), 7.12-7.06 (m, 2H), 5.47 (s, 2H), 4.22 (s, 2H). MS (DCI—NH3) m/z=356 (M+H)+.

Provenance & Evidence