Sodium Iodide → HCID 178443979, compound

Participants

Reaction Conditions

Reaction Steps

Part B. A 100 mL flask was charged with 2-mercaptoimidazo[4,5-b]-pyridine (0.65 g, 0.0043 mol), sodium iodide (0.129 g, 0.00086 mol), and potassium carbonate (0.789 g, 0.00571 mol) in N,N-dimethylformamide (15 mL). A solution of N-(5-bromopentyl)-N-heptyl-N'-(2,4-difluorophenyl)urea (2.34 g, 0.00558 mol) in N,N-dimethylformamide (20 mL) was added and the mixture was heated to 60° C. under nitrogen atmosphere for 18 hours, then cooled and poured into ethyl acetate (100 mL). The ethyl acetate solution was washed with water (3×100 mL), dried over magnesium sulfate and concentrated. Purification by flash chromatography of the resulting residue afforded the product, which solidified upon standing overnight. The residue was recrystallized to afford the title compound (2.13 g, 0.0043 mol) as a viscous oil. 1H NMR (CDCl3) δ8.27 (dd,1H,J=5.2, 1.4 Hz), 8.06-7.98 (m,1H), 7.91 (dd,1H,J=7.9, 1.3 Hz), 7.18 (dd,1H,J=7.9, 4.9 Hz), 6.84-6.76 (m,1H), 6.49 (d,1H,J=3.3 Hz), 3.41-3.24 (m,6H), 1.94-1.84 (m,2H), 1.74-1.51 (m,6H), 1.35-1.23 (m,8H), 0.88 (t,3H,J=6.6 Hz).

Provenance & Evidence