Cross-Coupling Reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine Offers a New Synthetic Route to Mutagenic Heterocyclic Amine-PHIP and DMIP

Sajith, Ayyiliath M.; Muralidharan, Arayambath; Karuvalam, Ranjith P.; Haridas, Karickal R.

doi:10.5012/jkcs.2013.57.3.361

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Cross-Coupling Reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine Offers a New Synthetic Route to Mutagenic Heterocyclic Amine-PHIP and DMIP

Journal title : Journal of the Korean Chemical Society
Volume 57, Issue 3, 2013, pp.361-364
Publisher : Korean Chemical Society
DOI : 10.5012/jkcs.2013.57.3.361

Title & Authors

Cross-Coupling Reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine Offers a New Synthetic Route to Mutagenic Heterocyclic Amine-PHIP and DMIP
Sajith, Ayyiliath M.; Muralidharan, Arayambath; Karuvalam, Ranjith P.; Haridas, Karickal R.;

Abstract

A modified synthetic approach to the synthesis of heterocyclic food mutagens, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PHIP) and 2-amino-1,6-dimethylimidazo[4,5-b]pyridine (DMIP) is reported. This route highlights an optimized palladium catalysed Buchwald cross-coupling of 2-halo-1-methyl-imidazo[4,5-b]pyridine with benzophenoneimine followed by acidic hydrolysis to yield compound 7. Using finely tailored conditions, Suzuki cross-coupling reactions with highly efficient catalytic systems were performed as the final step on 8 to introduce the aryl group and methyl group on the heterocyclic core.

Keywords

Buchwald coupling;Imidazopyridine;Suzuki coupling;Heterocyclic amines;

Language

English

Cited by

7time(s) in CrossRef

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