Cochennec, Corinne published the artcileMetalation of aryl iodides. Part II. Directed ortho-lithiation of 3-iodo-N,N-diisopropyl-2-pyridinecarboxamide: halogen-dance and synthesis of an acyclic analog of meridine, Safety of (2-Pivalamidophenyl)boronic acid, the publication is Synthesis (1995), 321-4, database is CAplus.
Metalation of the title iodopyridine was successfully achieved. Lithiation was ortho-directed by the iodo group which subsequently ortho-migrates to give a more stabilized iodolithiopyridine. An intermediate 4-lithio derivative could be trapped with chlorotrimethylsilane before iodo migration had occurred. The final 3-lithio compound was obtained in high yield which was reacted with electrophiles leading to various polysubstituted pyridines. The reaction was used for the preparation of an acyclic analog of meridine (I), a new marine alkaloid.
Synthesis published new progress about 146140-95-6. 146140-95-6 belongs to amides-buliding-blocks, auxiliary class Boronic acid and ester,Amine,Benzene,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (2-Pivalamidophenyl)boronic acid, and the molecular formula is C11H16BNO3, Safety of (2-Pivalamidophenyl)boronic acid.
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