Sodium Azide → HCID 86662233, compound

Participants

Reaction Steps

To a solution of 3-(3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)phenoxy)propyl methanesulfonate (470 mg, 0.72 mmol) in DMF (3 mL) at 0° C. was added NaN3 (186 mg, 2.87 mmol). After stirring for 16 h, the mixture was partitioned in EtOAc (20 mL) and water (20 mL). The separated organic layer was washed with 1M HCl (10 mL) and water (10 mL) successively, dried over MgSO4, filtered and evaporated. The mixture was purified by column chromatography (EtOAc/Hex=1:3) to provide 2-(4-(3-azidopropoxy)-2-chloro-6-fluorobenzylthio)-5-(2-(4-fluoro-3-methoxyphenyl)-propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (344 mg, 80% yield) as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.21 (s, 1H), 6.87 (dd, J=10.99, 8.49 Hz, 1H), 6.76 (t, J=8.49 Hz, 2H), 6.67 (s, 1H), 6.58 (dd, J=8.15, 2.15 Hz, 1H), 6.52-6.42 (m, 2H), 6.38-6.29 (m, 2H), 4.16 (t, J=4.34 Hz, 2H), 3.98 (t, J=5.89 Hz, 2H), 3.77 (d, J=5.67 Hz, 3H), 3.50 (t, J=6.51 Hz, 2H), 2.17 (s, 1H), 2.13-1.97 (m, 3H), 1.60 (s, 2H), 1.49 (s, 6H).

Provenance & Evidence