Synthesis of 5-bromopyridyl-2-magnesium chloride and its application in the synthesis of functionalized pyridines

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4905-4907

  Song, Jinhua J ^a   Yee, Nathan K ^a   Tan, Zhulin ^a   Xu, Jinghua ^a   Kapadia, Suresh R ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 BROMOPYRIDYL 2 MAGNESIUM CHLORIDE; ANTINEOPLASTIC AGENT; CHLORIDE; LONAFARNIB; MAGNESIUM; PYRIDINE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS;

MAGNESIUM CHLORIDE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PYRIDINES;

EID: 12344249681     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0400589     Document Type: Article

References (19)

1. Parham, W. E.; Piccirlli, R. M. J. Org. Chem. 1977, 42, 257.
2. Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169.
3. (a) Romero-Salguero, F. J.; Lehn, J.-M. Tetrahedron Lett. 1999, 40, 859.
4. (b) Wicha, J.; Masnyl, M. Heterocycles 1981, 16, 521.
5. (c) Alderweireldt, F. C.; Vrijens, I., Esmans, E. L.; Wotring, L. L.; Townsend, L. B.; Balzarini, J.; De Clereq, E. Nucleosides Nucleotides 1989, 8, 891.
6. Wang, X.; Rabbat, P.; O'Shea, P.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 2000, 41, 4335.
7. Trecourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Queguiner, G. Tetrahedron Lett. 1999, 40, 4339.
8. Mase, T.; Houpis, I. N.; Akao, A.; Dorziotis, I. K.; Hoang, T.; Iida, T.; Itoh, T.; Kamei, K.; Kato, S.; Kato, Y.; Kawasaki, M.; Lang, F.; Lee, J.; Lynch, J.; Maligres, P.; Monila, A.; Nemoto, T.; Okada, S.; Reamer, R.; Song, J. Z.; Tschaen, D.; Wada, T.; Zewge, D.; Volante, R. P.; Reider, P. J.; Tomimoto, K. J. Org. Chem. 2001, 66, 6775.
9. Song, J. J.; Yee, N. K. J. Org. Chem. 2001, 66, 605.
10. 4 (400 g) for 30 min and filtered. Evaporation of solvents gave 589 g (90% yield) of the desired aldehyde (3a) as a brownish-yellow solid.
11. (a) Couve-Bonnaire, S.; Carpentier, J.-F.; Mortreux, A.; Castanet, Y. Tetrahedron 2003, 59 (16), 2793.
12. (b) Couve-Bonnaire, S.; Carpentier, J.-F.; Mortreux, A.; Castanet, Y. Tetrahedron Lett. 2001, 42 (22), 3689.
13. Markevitch, D. Y.; Rapta, M.; Hecker, S. J.; Renau, T. E. Synth. Commun. 2003, 33, 3285.
14. Boschelli, D. H.; Wang, Y.; Boschelli, F. C.; Berger, D. M.; Zhang, N.; Powell, D. W.; Ye, F.; Yamashita, A.; Demorin, F. F.; Wu, B.; Tsou, H.-R.; Overbeek-Klumpers, E. G.; Wissner, A. U.S. Patent 2002026052, 2002.
15. Abramovitch, R. A.; Helmer, F.; Liveris, M. J. Org. Chem. 1969, 34, 1730.
16. 5-Bromo-2-iodo-3-picoline (6) was synthesized according to the general method in ref 7 (see Supporting Information).
17. (a) Kuo, S.-C.; Chen, F.; Hou, D.; Kim-Meade, A.; Bernard, C.; Liu, J.; Levy, S.; Wu, G. G. J. Org. Chem. 2003, 68, 4984.
18. (b) Poirier, M.; Chen, F.; Bernard, C.; Wong, Y.-S.; Wu, G. G. Org. Lett. 2001, 3, 3795.
19. (c) Wu, G. G.; Wong, Y.-S.; Poirier, M. Org. Lett. 1999, 1, 745.