4-Pyridinecarbothioamide → 4-(4-Fluorophenyl)-5-(4-methylthiophenyl)-2-(4-pyridyl)thiazole

Participants

Reaction Steps

A solution of the intermediate from Example 1, Step 3, 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone, (1.58 g, 4.66 mmol) and thioisonicotinamide (670 mg, 4.84 mmol) in 25 mL of acetonitrile was heated to reflux for 23 hours. The solution was filtered, concentrated in vacuo and the residue taken up in dichloromethane. The dichloromethane solution was washed with sat. aq. NaHCO3, and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give a brown oil that was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane to provide the desired thiazole as an oil that solidified upon standing (640 mg, 36%): mp 107°-109° C. 1H NMR (CDCl3) 300 MHz 8.75 (br s, 2H), 7.85 (d, J=5.9 Hz, 2H), 7.56 (m, 2H), 7.26 (d, J=8.5 Hz, 2H), 7.22 (d, J=8.5 Hz, 2H), 7.01 (t, J=8.5 Hz, 2H), 2.50 (s, 3H); 19F NMR (CDCl3) -113.23 (m). High resolution mass spectrum Calc'd. for C21H15FN2S2 : 379.0661. Found: 379.0691.

Provenance & Evidence