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The synthesis of 4‐benzylamino‐6‐methyl‐1 H ‐pyrrolo[3, 2‐ c ]pyridine and 4‐benzylamino‐6‐methyl‐1 H ‐pyrrolo[2, 3‐ b ]pyridine
Author(s) -
Meade Eric A.,
Beauchamp Lilia M.
Publication year - 1996
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.5570330215
Subject(s) - chemistry , pyridine , stereochemistry , medicinal chemistry
4‐Benzylamino‐6‐methyl‐1 H ‐pyrrolo[3,2‐ c ]pyridine ( 2 ) and 4‐benzylamino‐6‐methyl‐1 H ‐pyrrolo[2,3‐ b ]pyridine ( 3 ) were synthesized as deaza analogues of the anxiolytic agent 4‐benzylamino‐2‐methyl‐7 H ‐pyrrolo[2,3‐ d ]pyrimidine ( 1 ). The 1‐deaza analogue (2) was prepared via a multi‐step procedure from a pyrrole precursor, 1‐benzyl‐2‐formylpyrrole ( 4 ) while the 3‐deaza analogue 3 was synthesized from a pyridine precursor, 2‐amino‐3,6‐dimethylpyridine ( 12 ).