Sodium Iodide → N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine

Participants

Reaction Steps

A solution of 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (230 mg, 0.502 mmol), sodium iodide (376 mg, 2.51 mmol), and diisoproplylethylamine (0.088 mL, 0.50 mmol) in acetone (10 mL) was heated in a sealed vessel at 100° C. for 2 h. The reaction was concentrated in vacuo. The crude product was purified using silica gel column chromatography (10-80% EtOAc/chloroform, linear gradient) to afford 67 mg (30% yield) of the titled compound as a pink solid. LC-MS (M+H)+ 422.3. 1H NMR (500 MHz, chloroform-d) δ ppm 7.93 (s, 1H) 7.65 (dd, J=12.51, 2.44 Hz, 1H) 721-7.24 (m, 1H) 7.09-7.16 (m, 2H) 6.99-7.08 (m, 3H) 6.90 (s, 1H) 4.21-4.31 (m, 3H) 2.37 (s, 3H) 2.15-2.26 (m, 1H) 2.03-2.12 (m, 1H) 1.81-2.01 (m, 4H).

Provenance & Evidence