1,1'-Thiocarbonyldi-2(1H)-pyridone → 2-(4-chloro-1H-imidazol-1-yl)-5-isothiocyanato-3-methoxypyridine

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Reaction Steps

Step O (3): Dichloromethane (100 mL) was added to a flask charged with 6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-amine (3.0 g, 13.35 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (3.10 g, 13.35 mmol). The resulting mixture was stirred for 18 h at rt. The reaction mixture was concentrated in vacuo. The crude products were purified using silica gel chromatography (0-5% EtOAc/chloroform, linear gradient) to afford 2-(4-chloro-1H-imidazol-1-yl)-5-isothiocyanato-3-methoxypyridine (2.89 g, 81% yield) as a yellow solid. LC-MS (M+H)+ 267.1. 1H NMR (500 MHz, chloroform-d) δ ppm 8.30 (s, 1 H) 8.02 (s, 1 H) 7.72 (s, 1 H) 7.20 (s, 1 H) 4.00 (s, 3 H).

Provenance & Evidence