2-Aminopyridine → 2-Chloromethyl-imidazo(1,2-A)pyridine

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Reaction Steps

[step 1] To commercially available 2-aminopyridine (5.0 g, 53 mmol) were added dimethoxyethane (14 mL) and 1,3-dichloropropanone (7.4 g, 58 mmol), and the mixture was stirred at room temperature overnight. The obtained white crystals were collected by filtration, ethanol (140 mL) was added, and the mixture was stirred with heating under reflux for 1 hr. The reaction was discontinued with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with chloroform and the extract was dried over sodium sulfate. Filtration and concentration under reduced pressure gave 2-(chloromethyl)imidazo[1,2-a]pyridine (5.5 g, 62%).

Provenance & Evidence