Thionicotinamide → HCID 22912196, compound

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone from Step 2 (0.732 g, 1.97 mmol) in acetonitrile (20 mL) in a 50 mL round bottom flask was added thionicotinamide (0.273 g, 1.97 mmol) with stirring. The resulting solution was heated to reflux for 1 hour and additional 2-bromo-1-(4-fluorophenyl)-3-(methylsulfonylphenyl)ethanone (0.031 g, 0.05 mmol) was added and stirred at ruflux for an additional hour. The reaction was cooled to room temperature and concentrated in vacuo yielding an orange semi-solid. This was purified by flash chromatography (2:1 hexane:ethyl acetate with 1% acetic acid). The product fractions were combined, toluene added, and the resulting solution reconcentrated in vacuo yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3-pyridyl) thiazole as a pale yellow crystalline solid (0.351 g, 43%): mp 143°-146° C. 1H NMR (CDCl3) 400 mHz δ9.20 (d, J=1.81 Hz, 1H), 8.68 (dd, J=1.46, 4.89 Hz, 1H), 8.30 (dr, J=2.00, 9.42 Hz, 1H), 7.91 (d, J=8.55 Hz, 2H), 7.60-7.52 (m, 4H), 7.42 (m, 1), 7.05 (t, J=8.70 Hz, 2H), 3.10 (s, 3H). MS (EI): m/z 410 (M+). HRMS Δ=-4.3

Provenance & Evidence