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Short Paper | Special issue | Vol 99, No. 2, 2019, pp.1342-1354
Published online, 25th January, 2019
DOI: 10.3987/COM-18-S(F)64
Problem of Regioselectivity in the Amination of 2-Fluoro-5-iodopyridine with Adamantylalkyl Amines

Anton S. Abel, Yury N. Kotovshchikov, Alexei D. Averin,* Olga A. Maloshitskaya, Evgenii N. Savelyev, Boris S. Orlinson, Ivan A. Novakov, and Irina P. Beletskaya

*Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991, Moscow, Russia

Abstract

Cu(I)-Catalyzed and catalyst-free amination of 2-fluoro-5-iodopyridine with adamantylalkyl amines possessing different steric hindrances at amino group was investigated to obtain corresponding 5-amino-2-fluoro- and 2-amino-5-iodopyridines. The competition between catalytic substitution of iodine and non-catalytic substitution of fluorine was shown to take place. The catalytic system CuI/2-(isobutyryl)cyclohexanone in DMF provided yields of 5-amino-2-fluoropyridines up to 58% with stoichiometric ratio of the reagents and up to 98% with two equiv. of amines. The non-catalytic amination of 2-fluoro-5-iodopyridine provided the yields of 2-amino-5-iodopyridines up to 97%.