Iodine → 6-Iodo-3-(4-methoxyphenyl)-2-methylpyridine

Participants

Reaction Conditions

Reaction Steps

5-(4-methoxyphenyl)-6-methylpyridin-2-amine (500 mg, 2.33 mmol) and iodine (710 mg, 2.8 mmol) were stirred in chloroform (10 mL) at room temperature for 12 minutes followed by addition of n-amyl nitrite (545.9 mg, 4.66 mmol). The resulting mixture was heated in a 82° C. oil bath for 1.5 hours to finish the transformation. The reaction was quenched by addition of saturated NaS2O3 aqueous solution. The reaction mixture was extracted with dichloromethane. The combined organic extracts were dried over Na2SO4 followed by filtration and concentration. The resulting crude was purified by flash column chromatography on SiO2 (Biotage 40+M cartridge, dichloromethane/hexanes, gradient) to afford a yellow oil. The oil was further purified by preparative TLC on SiO2 (eluted with 80% dichloromethane in hexanes) to afford 6-iodo-3-(4-methoxyphenyl)-2-methylpyridine. LCMS calc.=325.00; found=326.06 (M+1)+.

Provenance & Evidence