2,3-Dihydro-1H-Pyrrolo[3,4-C]Pyridine dihydrochloride

Application

2,3-Dihydro-1H-pyrrole[3,4-C]pyridine dihydrochloride can be used as a pharmaceutical synthesis intermediate and can be prepared from propargylamine and ethyl chloroformate through a four-step reaction. Literature reports its potential use in the preparation of an A2A receptor antagonist.

Synthesis

a. Propargylamine reacts with ethyl chloroformate to give ethyl N-propargylcarbamate.
b. The product from step a reacts with 2-chloromethylpyrimidine to yield 2-(N-ethoxycarbonyl-N-propargylaminomethyl)pyrimidine.
c. The product from step b undergoes cyclization by refluxing in xylene to give ethyl 5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate.
d. The ester from step c is hydrolyzed/decarboxylated in conc. HCl to yield 2,3-dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride.