N-Alkylation of Some Imidazopyridines

6-Bromo-2-(4-(4-fluorophenoxy)phenyl)-4H-imidazo[4,5-b]pyridine (I) and 2-[4-(4-fluorophenoxy)phenyl]-5H-imidazo[4,5-c]pyridine (III) were prepared by the reaction of 5-bromo-2,3-diaminopyridine and 3,4-diaminopyridine with sodyum metabisulfite adduct of 4-(4-fluorophenoxy)benzaldehyde (1), respectively. Alkylation of these compounds with 1-(chloromethyl)-4-methoxybenzene under basic conditions (K2CO3) in DMF) were formed as mainly N4 regioisomer (II) and N5 regioisomer (IV). Their regioisomeric structures were assigned with 2D-NOESY (Nuclear Overhauser Effect Spectroscopy) spectra.

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Publication Details

Journal
Fabad Journal of Pharmaceutical Sciences
Published
2025-03-25
DOI
https://doi.org/10.55262/fabadeczacilik.1577453
Primary Topic
Synthesis of heterocyclic compounds
Type
article
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article

N-Alkylation of Some Imidazopyridines

Hakan Göker, Fatıma Doğanç
Fabad Journal of Pharmaceutical Sciences
Synthesis of heterocyclic compounds
article

N-Alkylation of Some Imidazopyridines

Hakan Göker, Fatıma Doğanç
article en

Abstract

6-Bromo-2-(4-(4-fluorophenoxy)phenyl)-4H-imidazo[4,5-b]pyridine (I) and 2-[4-(4-fluorophenoxy)phenyl]-5H-imidazo[4,5-c]pyridine (III) were prepared by the reaction of 5-bromo-2,3-diaminopyridine and 3,4-diaminopyridine with sodyum metabisulfite adduct of 4-(4-fluorophenoxy)benzaldehyde (1), respectively. Alkylation of these compounds with 1-(chloromethyl)-4-methoxybenzene under basic conditions (K2CO3) in DMF) were formed as mainly N4 regioisomer (II) and N5 regioisomer (IV). Their regioisomeric structures were assigned with 2D-NOESY (Nuclear Overhauser Effect Spectroscopy) spectra.

Fabad Journal of Pharmaceutical SciencesVol. 50(1)
Ankara University (TR), Cecil College (US)
Openalex Percentile: Top 96%
Synthesis of heterocyclic compounds
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