- Efficient synthesis of substituted imidazo[4,5-b] pyridine
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An efficient approach to the synthesis of 1-methylimidazo[4,5-b]pyridine derivatives 5-10 of biological interest has been developed. The key intermediate product 4 is obtained by cyclization of 2-amino-3-methylaminopyridine (3) with phenylacetic acid.
- Xing, Yuan-Yuan,Liu, Chuanxiang,Wu, Fanhong
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- Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues
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In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.
- Savitha, Bhaskaran,Sajith, Ayyiliath. M.,Joy, M. Nibin,Khader, K.K. Abdul,Muralidharan,Padusha, M. Syed Ali,Bodke, Yadav D.
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p. 618 - 630
(2016/07/06)
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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
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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.
- Sajith, Ayyiliath M.,Muralidharan, Arayambath,Karuvalam, Ranjith P.,Haridas, Karickal R.
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p. 361 - 364
(2013/07/26)
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- CYCLOHEXYL AMIDE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS
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There are described cydohexyl amide derivatives useful as corticotropin releasing factor (CRF) receptor antagonists
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Page/Page column 93-94
(2016/02/02)
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- AZABENZIMIDAZOLYL COMPOUNDS
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Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I), as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
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Page/Page column 58
(2008/06/13)
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- 3-(Imidazolyl methyl)-3-aza-bicyclo[3.1.0]hexan-6-yl)methyl ethers: A novel series of mGluR2 positive allosteric modulators
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The synthesis and structure-activity relationship (SAR) of a novel series of 3-(imidazolyl methyl)-3-aza-bicyclo[3.1.0]hexan-6-yl)methyl ethers, derived from a high throughput screening (HTS), are described. Subsequent optimization led to identification of potent, metabolically stable and orally available mGluR2 positive allosteric modulators (PAMs).
- Zhang, Lei,Rogers, Bruce N.,Duplantier, Allen J.,McHardy, Stanley F.,Efremov, Ivan,Berke, Helen,Qian, Weimin,Zhang, Andy Q.,Maklad, Noha,Candler, John,Doran, Angela C.,Lazzaro Jr., John T.,Ganong, Alan H.
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scheme or table
p. 5493 - 5496
(2009/06/18)
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