Sodium Iodide → HCID 58110118, compound

Participants

Reaction Steps

A solution of 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (2.00 g, 3.81 mmol), sodium iodide (2.90 g, 19.1 mmol), and diisoproplylethylamine (3.33 mL, 19.1 mmol) in acetone (25 mL) was heated in a sealed vessel at 100° C. for 6 h. The reaction was concentrated in vacuo. Water (250 mL) was added and the mixture was extracted with EtOAc (2×250 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified using silica gel column chromatography (70% EtOAc/chloroform) to afford 350 mg (19% yield) of the titled compound as a white solid. LC-MS (M+H)+ 488.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.96 (s, 1 H), 7.68 (dd, J=12.7, 2.3 Hz, 1 H), 7.26-7.29 (m, 1 H), 7.19-7.25 (m, 4 H), 7.04 (dd, J=8.9, 2.1 Hz, 1H), 6.87 (s, 1 H), 4.31 (dd, J=8.9, 2.4 Hz, 1 H), 4.27 (t, J=5.0 Hz, 2 H), 2.39 (s, 3 H), 2.17-2.29 (m, 1 H), 2.06-2.16 (m, 1 H), 1.84-2.04 (m, 4 H).

Provenance & Evidence