Synthesis of 2-amino-3-hydroxy-4-substituted pyridines via regioselective metalation of 3-(1-ethylpropyl)-[1,3]oxazolo[4,5-b]pyridin-2(3H)-one and application to corticotropin releasing factor1 receptor ligands |
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Authors: | Richard A. Hartz Kausik K. Nanda |
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Affiliation: | a Discovery Chemistry, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, CT 06492, USA b Merck Research Laboratories, West Point, PA 19486, USA c Wyeth, Pearl River, NY 10965, USA |
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Abstract: | An efficient route to the preparation of 2-amino-3-hydroxy-4-substituted pyridines is described. The key step involves the regioselective metalation and subsequent alkylation of the [1,3]oxazolo[4,5-b]pyridin-2(3H)-one ring system. Base hydrolysis provides access to a variety of 4-substituted pyridines. This chemistry is proved to be useful for the synthesis of corticotropin releasing factor1 receptor ligands. |
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Keywords: | Regioselective metalation Pyridine Corticotropin releasing factor |
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