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Silver(I)-assisted electrophilic aromatic iodination of commercially available 5-aminopicolinonitrile 2 gave the mono-iodinated intermediate 3 in 79% yield. In mild and efficient DBU-catalyzed amidation of cyanoacetates activation of the α-carboxyl group allowed condensation with 5-amino-2-cyanopyridine.
Hannes Koolmanb,; Timo Heinricha,; Henning Böttchera,; Wilfried Rautenberga,; Michael Reggelin. Syntheses of novel 2,3-diaryl-substituted 5-cyano-4-azaindoles exhibiting c-Met inhibition activity. Bioorganic & Medicinal Chemistry Letters. 2009 , 19(7), 1879-1882.
Kristin E. Price,; Claude Larrivée-Aboussafy,; Brett M. Lillie,; Robert W. McLaughlin,; Jason Mustakis,; Kevin W. Hettenbach,; Joel M. Hawkins,;Rajappa Vaidyanathan. Mild and Efficient DBU-Catalyzed Amidation of Cyanoacetates. Org. Lett. 2009, 11 (9),2003-2006.
Hazard Statements: H301-H311-H319
Toxic if swallowed. Toxic in contact with skin. Causes serious eye irritation.
Precautionary Statements: P280f-P305+P351+P338-P309-P310a
Wear protective clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: