Hydrochloric Acid → Ethyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

30 ml of n-butyllithium are added, under nitrogen, at a temperature of less than 5° C., to 5 g of 2-(N-Boc)amino-3-methylpyridine in 100 ml of THF. After stirring for 1 hour at 0° C., the lithiated derivative thus formed is added to a solution of 7 g of ethyl oxalate in 50 ml of THF at −3° C. The reaction medium is allowed to return to RT and is then poured slowly into 25 ml of 6N HCl at 0° C., while maintaining the temperature below 100° C. This mixture is heated at 50° C. for 2 hours and the pH is then brought to 3 by addition of 1N NaOH. This mixture is extracted with Et2O and the organic phase is taken up in K2CO3 solution and then dried and evaporated to give 1.8 g of the expected compound in the form of white crystals: m.p.=162° C.

Provenance & Evidence