Cesium fluoride → 3-[4-[2-(benzyloxy)ethyl]phenyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine

Participants

Reaction Conditions

Reaction Steps

A solution/suspension of 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (427 mg, 1.00 mmol), 1-[2-(benzyloxy)ethyl]-4-iodobenzene (338 mg, 1.00 mmol), CsF (304 mg, 2.00 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol) and CuI (19 mg, 0.10 mmol) in anhydrous DMF (5 mL) was stirred at 50° C. for 5 h under N2. The reaction mixture was cooled and concentrated under vacuum. The residue was applied onto a silica gel column, and the product was eluted with EtOAc/petroleum ether/Et3N 3:6:0.5 as the eluent to give the title compound (280 mg, 59%) as light-yellow oil. 1H NMR (CDCl3, 300 MHz) δ 8.48 (s, 1H), 8.33 (d, J=2.1 Hz, 1H), 7.55 (d, J=8.1 Hz, 2H), 7.48 (s, 1H), 7.37-7.29 (m, 7H), 4.57 (s, 3H), 4.42 (s, 1H), 4.24 (dd, J=7.2, 3.0 Hz, 1H), 3.93 (t, J=7.2 Hz, 2H), 3.75 (t, J=7.2 Hz, 2H), 3.00 (t, J=7.2 Hz, 2H), 2.43-2.30 (m, 2H), 1.42 (s, 9H). LC-MS (ESI) m/z 475 (M+H+).

Provenance & Evidence