4-Iodo-1-tritylimidazole → HCID 178423886, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-Iodo-1-trityl-1H-imidazole (1 eq) in THF at room temperature was added ethylmagnesium bromide (1.2) under dry conditions. After stirring for 90 minutes, zinc chloride (1.2 eq) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis(triphenylphosphine)palladium (10%) and 5-bromo-2-methylpyridine (1.2 eq) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70° C. oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane and washed with a EDTA buffer (at pH˜9), NaCl(sat), dried over sodium sulfate, filtered and concentrated. The crude product was dissolved in ethanol and concentrated HCl was added to the solution at room temperature. The reaction mixture was heated in a 50° C. oil bath for 2 hours. Upon cooling, the reaction was filtered and washed with ethyl ether to yield 5-(1H-Imidazol-4-yl)-2-methyl-pyridine (63%). MH+(160).

Provenance & Evidence