Pyridine → 4-(Trifluoromethyl)thiazole-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of anhydrous DMF (18.5 mL, 1.3 eq.) in acetonitrile (460 mL) was added a 2M solution of oxalyl chloride in DCM (118 mL, 1.3 eq.) dropwise at 0° C. After the mixture was stirred for 30 min at 0° C., a solution of compound 285a (35.5 g, 1.0 eq.) and pyridine (14.5 mL, 1.0 eq.) in acetonitrile (180 mL) was added. The reaction mixture was stirred at room temperature for 3 hrs. The mixture was concentrated in vacuo. The residue obtained was dissolved in EtOAc (400 mL) and washed with H2O (4×300 mL). Organics were dried over MgSO4, filtered, and concentrated in vacuo to yield compound 285b as a brown oil in 87% yield. 1H NMR (CDCl3, 400 MHz) δ 8.15 (s, 1H).

Provenance & Evidence