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3-Acetylamino-5-ethoxypyridine was prepared by converting 3, 5-dibromopyridine with sodium ethylate into 3-bromo-5-ethoxypyridine, allowing this substance to interact with ammonia and acetylating the aminoethoxypyridine thus formed with acetic anhydride. Lithiation of 3, 5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3, 5-dibromopyridines 2 in high yield. Ligand was prepared by a Pd(0)-catalyzed cross-coupling reaction of 3,5-dibromopyridine and 5-tributylstannyl-3,3?-bipyridine. The synthesis of 3, 5-bis (2-indolyl) pyridine and 3-[(2-indolyl)-5-phenyl] pyridine derivatives as includes Stille or Suzuki type reactions, which were realized on the 3,5-dibromopyridine.
V. Krishnakumar,; R.John Xavier. Density functional theory calculations and vibrational spectra of 3,5-dibromopyridine and 3,5-dichloro-2,4,6-trifluoropyridine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2005, 61(1-2), 253-260.
Alexandre Bouillon,; Jean-Charles Lancelot,; Valérie Collot,; Philippe R Bovy,; Sylvain Rault. Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters . Tetrahedron. 2002 , 58(17), 3323-3328.
With n-BuLi at -30 o, selective metallation occurs by exchange with one Br atom: J. Org. Chem., 16,1485 (1951). In contrast, using LDA in THF at -100 o, lithiation can be accomplished at the 4-position. Subsequent reaction with an electrophile can be followed by lithiation with n-BuLi to give 3-bromo-4,5-disubstituted pyridines: Tetrahedron Lett ., 37, 2565 (1996):
Hazard Statements: H301-H311-H332-H315-H319-H335
Toxic if swallowed. Toxic in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280-P301+P310a-P305+P351+P338-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.