Toluene → HCID 72218342, compound

Participants

Reaction Conditions

Reaction Steps

A pressure vial was charged with 3-(trifluoromethyl)-1,7-naphthyridin-8(7H)-one (Anichem) (75 mg, 0.350 mmol), toluene (1401 μl), and Hunig's base (184 μl, 1.051 mmol). To this mixture was added POCl3 (98 μl, 1.051 mmol), and the vial was sealed. The reaction was heated at 115° C. for 2 h. After 6 h, some unreacted starting material remained. The temperature was increased to 125° C. and the reaction was stirred overnight. Upon cooling to RT, EtOAc and water were added, and the layers were separated. The aqueous portion was extracted with additional EtOAc, and the combined organic portions were dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography using a gradient of 0-50% EtOAc in heptane to provide 8-chloro-3-(trifluoromethyl)-1,7-naphthyridine (78 mg, 0.335 mmol, 96%) as a tan solid. LC/MS (ESI+) m/z=233.1 (M+H).

Provenance & Evidence