Sodium Iodide → 3-{4-[(3-Aminopropyl)amino]-1,2,5-oxadiazol-3-yl}-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-{4-[(3-azidopropyl)amino]-1,2,5-oxadiazol-3-yl}-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (2.0 g, 4.7 mmol) in methanol (36 mL) was treated with sodium iodide (4.2 g, 28 mmol) and stirred at 25° C. for 5 min. The reaction mixture was treated with a solution of chlorotrimethylsilane (3.6 mL, 28 mmol) in methanol (7 mL) dropwise and stirred at 25° C. for 40 min. The reaction mixture was slowly poured into a solution of sodium thiosulfate (5.0 g, 32 mmol) in water (200 mL) that was cooled at 0° C. The solid that precipitated was filtered, washed with water, and dried to give the desired product (2.3 g, 93%) as a solid. LCMS for C13H13BrFN6O3 (M+H)+: m/z=399.0, 401.0. 1HNMR (400 MHz, DMSO-d6): δ 8.08 (dd, J=6.1, 2.3 Hz, 1 H), 7.74-7.70 (m, 1 H), 7.60 (dd, J=8.8, 8.6 Hz, 1 H), 7.22 (br s, 2 H), 6.69 (br s, 1 H), 2.81-2.77 (m, 2H), 1.86-1.79 (m, 2 H).

Provenance & Evidence