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Ortho-lithiation with t-BuLi of the Boc-protected amine followed by addition of a Weinreb amide gave the 2-alkyl substituted 5-azaindole in good yield: J. Heterocycl. Chem., 29, 359 (1992), whereas DMF gave 6-azaindole in high yield: Synthesis, 877 (1996). 2-Substituted 6-azaindoles have also been synthesized in one step by direct dilithiation with s-BuLi, followed by reaction with an ester: J. Org, Chem., 70, 6512 (2005)./n
Hazard Statements: H302-H315-H318-H335
Harmful if swallowed. Causes skin irritation. Causes serious eye damage. May cause respiratory irritation.
Precautionary Statements: P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P310-P312-P330-P332+P313-P362-P501c
Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant