Sodium Iodide → N-[3-(1-{5-[4-(3,4-Difluorophenyl)-2-oxo-1,3-oxazolidin-3-YL]pentyl}-4-piperidinyl)phenyl]-2-methylpropanamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(5-bromopentyl)-4-(3,4-difluorophenyl)-1,3-oxazolidin-2-one (38.0 mg, 0.110 mmol), 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide (26.0 mg, 0.100 mmol), NaI (23.0 mg, 0.150 mmol), and K2CO3 (14.0 mg, 0.100 mmol) in DMF (2 mL) was heated for 1 h at 50° C. The crude product was purified by preparative TLC using CH2Cl2/MeOH/isopropyl amine (19:1:0.2) to give the desired product (21 mg, 41%). 1H NMR (400 MHz, CDCl3) δ 7.49 (s, 1H), 7.39–7.32 (m, 2H), 7.26–7.20 (m, 2H), 7.18–7.11 (m, 1H), 7.10–7.03 (m, 1H), 6.96 (d, 1H, J=7.6 Hz), 4.80–4.73 (m, 1H), 4.62 (t, 1H, J=7.9 Hz), 4.09–4.04 (m, 1H), 3.51–3.42 (m, 1H), 3.03 (d, 2H, J=11.7 Hz), 2.82–2.72 (m, 1H), 2.51–2.42 (m, 2H), 2.32 (t, 2H, J=7.9 Hz), 2.11 (s, 1H), 2.03–1.97 (m, 2H) 1.85–1.70 (m, 4H), 1.49 (m, 4H), 1.31–1.27 (m, 1H), 1.24 (d, 6H, J=6.9 Hz); ESMS m/e: 514.4 (M+H)+.

Provenance & Evidence