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A synthesis of 5‐carboxamidopyrrolo[3,2‐ b ]pyridine
Author(s) -
Macor John E.,
Post Ronald,
Ryan Kevin
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290616
Subject(s) - chemistry , pyridine , agonist , yield (engineering) , indole test , hydrolysis , pyridine n oxide , stereochemistry , 5 ht receptor , combinatorial chemistry , medicinal chemistry , serotonin , receptor , organic chemistry , biochemistry , materials science , metallurgy
A four‐step synthesis of 5‐carboxamidopyrrolo[3,2‐ b ]pyridine ( 3 ) from pyrrolo[3,2‐ b ]pyridine ( 4 ) is described (45% overall yield). The one‐step conversion of the N ‐oxide 6 of the pyrrolo[3,2‐ b ]pyridine 5 leads to the 5‐cyanopyrrolo[3,2‐ b ]pyridine 7. The cyano group is hydrolyzed to afford the title compound 3 , which is the 4‐aza analog of the indole backbone in 5‐carboxamidotryptamine, a potent agonist of the neurotransmitter, serotonin.
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