1,1'-Thiocarbonyldi-2(1H)-pyridone → 3-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

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Reaction Steps

To a solution of 3-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 15 (280 mg, 1 mmol) in DCM (5 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (233 mg, 1 mmol) at rt. The solvent was removed in vacuo after 1 h. The crude white solid of 3-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 19 was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.18 (d, J=8.0 Hz, 1H), 7.09 (dd, J=2.4, 8.0 Hz, 1H), 7.05 (d, J=2 Hz, 1H), 7.04 (s, 1H), 3.66 (s, 3H), 2.64 (s, 3H), 2.16 (s, 3H). MS m/z 322.2 (M+1).

Provenance & Evidence