Thermal amination of 2,6-dihalopyridines by sterically demanding amines

Synthesis

Volumn , Issue 1, 2009, Pages 155-159

  Faust, Andreas ^a   Wolff, Oliver ^b   Waldvogel, Siegfried R ^b  

^a UNIVERSITY HOSPITAL MÜNSTER   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Aminations; Nucleophilic aromatic substitutions; Pyridines; Steric hindrance; Tetramethylpiperidine

Indexed keywords

ACID-LABILE; AMINATION REACTIONS; AMINATIONS; CHLOROPYRIDINES; NUCLEOPHILIC AROMATIC SUBSTITUTIONS; STERIC HINDRANCE; STERICALLY DEMANDING; TETRAMETHYLPIPERIDINE;

AMINES; AROMATIC COMPOUNDS; PYRIDINE; TRANSITION METALS;

AMINATION;

2 (ADAMANTAN 1 YLAMINO) 6 BROMOPYRIDINE; 2 (ADAMANTAN 1 YLAMINO) 6 CHLOROPYRIDINE; 2 BROMO 6 (2,6 DIMETHYLPIPERIDIN 1 YL)PYRIDINE; 2 BROMO 6 (DIISOPROPYLAMINO)PYRIDINE; 2 BROMO 6 [(2,6 DIISOPROPYLPHENYL)AMINO]PYRIDINE; 2 BROMO 6 [(2,6 DIMETHYLPHENYL)AMINO]PYRIDINE; 2 BROMO 6 [{SPIRO(1,3 BENZODIOXOLE 2,9' BICYCLO(3.3.1)NONAN) 1 YL}AMINO)PYRIDINE; 2 CHLORO 6 (2,6 DIMETHYLPIPERIDIN 1 YL)PYRIDINE; 2 FLUORO 6 [{SPIRO(1,3 BENZODIOXOLE 2,9' BICYCLO(3.3.1)NONAN) 1' YL}AMINO]PYRIDINE; 2,2,6,6 TETRAMETHYLPIPERIDINE; 2,5 DIBROMOPYRIDINE; 2,6 BIS[(2,6 DIMETHYLPHENYL)AMINO]PYRIDINE; 2,6 DICHLOROPYRIDINE; 2,6 DIHALOPYRIDINE DERIVATIVE; AMINE; BROMINE DERIVATIVE; BROMOPYRIDINE DERIVATIVE; CHLOROPYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; STEREOSPECIFICITY; THERMAL ANALYSIS;

EID: 63849311584     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083268     Document Type: Article

References (30)

1. (a) Klebl, B.; Baumann, M.; Hoppe, E.; Brehmer, D.; Daub, H.; Keri, G.; Varga, Z.; Marosfalvi, J.; Oerfi, L. WO 2006,021,458, 2006.
2. (b) Chung, J. Y. L.; Cvetovich, R. J. Curr. Opin. Drug Discovery Dev. 2006, 9, 792.
3. (a) Babu, P. A.; Narasu, M. L.; Srinivas, K. ARKIVOC 2007, (ii), 247.
4. (b) De Clercq, E.; Naesens, L. J. Clin. Virol. 2006, 37, S82.
5. (c) Gassel, M.; Breitenlechner, C.; Herrero, S.; Engh, R.; Bossemeyer, D. Handbook of Experimental Pharmacology, Vol. 167; Pinna, L. A.; Cohen, P. T. W., Eds.; Springer: Heidelberg, 2005, 85.
6. Dalton King, H.; Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Epperson, J. R.; Higgins, M. A.; Kung, J. E.; Marcin, L. R.; Sloan, C. P.; Mattson, G. K.; Molski, T. F.; Krause, R. G.; Bertekap, R. L.; Lodge, N. J.; Mattson, R. J.; Macor, J. E. Bioorg. Med. Chem. Lett. 2007, 17, 5647.
7. Scholz, U.; Schlummer, B. In Science of Synthesis, Vol. 31; Ramsden, C., Ed.; Georg Thieme Verlag: Stuttgart, 2007, 1565.
8. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002,219, 131.
9. (b) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
10. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
11. (a) Kaila, N.; Green, N.; Li, H.; Hu, Y.; Janz, K.; Gavrin, L. K.; Thomason, J.; Tam, S.; Powell, D.; Cuozzo, J.; Hall, J. P.; Telliez, J.; Hsu, S.; Nickerson-Nutter, C.; Wang, Q.; Lin, L. Bioorg. Med. Chem. 2007, 15, 6425.
12. (b) Stoit, A. R.; den Hartog, A. P.; Mons, H.; van Schaik, S.; Barkhuijsen, N.; Stroomer, C.; Coolen, H. K. A. C.; Reinders, J. H.; Adolfs, T. J. P.; van der Neut, M.; Keizer, H.; Kruse, C. G. Bioorg. Med. Chem. Lett. 2008, 18, 188.
13. (c) Matsumoto, K.; Minatogawa, H.; Toda, M.; Munakata, M. Heterocycles 1990, 31, 1217.
14. (d) Laufer, S. A.; Hauser, D. R. J.; Liedtke, A. J. Synthesis 2008, 253.
15. (a) Modern Supramolecular Chemistry; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2008.
16. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: Chichester, 2000.
17. (a) Siering, C.; Kerschbaumer, H.; Nieger, M.; Waldvogel, S. R. Org. Lett. 2006, 8, 1471.
18. (b) Schopohl, M. C.; Siering, C.; Kataeva, O.; Waldvogel, S. R. Angew. Chem. Int. Ed. 2003, 42, 2620.
19. (c) Waldvogel, S. R.; Fröhlich, R.; Schalley, C. A. Angew. Chem. Int. Ed. 2000, 39, 2472.
20. (a) Schade, W.; Bohling, C.; Hohmann, K.; Bauer, C.; Orghici, R.; Waldvogel, S. R.; Scheel, D. Photonik Int. 2007, 1, 32.
21. (b) Orghici, R.; Willer, U.; Gierszewska, M.; Waldvogel, S. R.; Schade, W. Appl. Phys. B 2008, 90, 355.
22. Bomkamp, M.; Siering, C.; Landrock, K.; Stephan, H.; Frohlich, R.; Waldvogel, S. R. Chem. Eur. J. 2007, 13, 3724.
23. Katritzki, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry; Pergamon: London, 2003, 178.
24. Schopohl, M. C.; Mirk, D.; Faust, A.; Frohlich, R.; Kataeva, O.; Waldvogel, S. R. Eur. J. Org. Chem. 2005, 2987.
25. Faust, A. Ph.D. Thesis; University Munster: Germany, 2003.
26. 1H NMR spectroscopy.
27. Kampmann, D.; Stuhlmuller, G.; Simon, R.; Cottet, F.; Leroux, F.; Schlosser, M. Synthesis 2005, 1028.
28. Bacqué, E.; El Qacemi, M.; Zard, S. Z. Org. Lett. 2004, 6, 3671.
29. Maurin, J. K.; Lasek, W.; Gorska, A.; Switaj, T.; Jakubowska, A. B.; Kazimierczuk, Z. Chem. Biodiversity 2004, 1, 1498.
30. Kazimierczuk, Z.; Lasek, W.; Sikorska, A. WO 2001,074,778, 2001.