Regioselective halogenation of aminopyrimidinyl-pyrrole carboxylic acid derivatives

Tetrahedron

Volumn 65, Issue 50, 2009, Pages 10418-10423

  Vanotti, Ermes ^a   Caldarelli, Marina ^a   Disingrini, Teresa ^a   Nesi, Marcella ^a   Tatò, Marco ^a   Vianello, Paola ^a   Menichincheri, Maria ^a  

^a Nerviano Medical Sciences ^*  (Italy)

Author keywords

Halogenation; Kinase inhibitors; N Halosuccinimide; Pyrimidine; Pyrrole

Indexed keywords

5 (2 AMINO PYRIMIDIN 4 YL) 2 PHENYL 1H PYRROLE 3 CARBOXAMIDE; AMINOPYRIDINE DERIVATIVE; ETHYL 5 (2 AMINO 5 BROMO PYRIMIDIN 4 YL) 2 PHENYL 1H PYRROLE 3 CARBOXAMIDE; ETHYL 5 (2 AMINO 5 BROMO PYRIMIDIN 4 YL) 2 PHENYL 1H PYRROLE 3 CARBOXYLATE; ETHYL 5 (2 AMINO 5 BROMO PYRIMIDIN 4 YL) 4 IODO 2 PHENYL 1H PYRROLE 3 CARBOXAMIDE; ETHYL 5 (2 AMINO 5 CHLORO PYRIMIDIN 4 YL) 2 PHENYL 1H PYRROLE 3 CARBOXYAMIDE; ETHYL 5 (2 AMINO 5 CHLORO PYRIMIDIN 4 YL) 2 PHENYL 1H PYRROLE 3 CARBOXYLATE; ETHYL 5 (2 AMINO 5 IODO PYRIMIDIN 4 YL) 2 PHENYL 1H PYRROLE 3 CARBOXAMIDE; ETHYL 5 (2 AMINO 5 IODO PYRIMIDIN 4 YL) 2 PHENYL 1H PYRROLE 3 CARBOXYLATE; ETHYL 5 (2 AMINO 5 IODO PYRIMIDIN 4 YL) 4 IODO 2 PHENYL 1H PYRROLE 3 CARBOXAMIDE; ETHYL 5 (2 AMINO PYRIMIDIN 4 YL) 4 IODO 2 PHENYL 1H PYRROLE 3 CARBOXAMIDE; ETHYL 5 (2 AMINO PYRIMIDIN 4 YL) 4 IODO 2 PHENYL 1H PYRROLE 3 CARBOXYLATE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HALOGENATION; PRIORITY JOURNAL;

EID: 71049153725     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.030     Document Type: Article

References (33)

1. Akritopoulou-Zanze I., and Hajduk P.J. Drug Discov. Today 14 (2009) 291
2. Campeau L.-C., Stuart D.R., Leclerc J.-P., Bertrand-Laperle M., Villemure E., Sun H.-Y., Lasserre S., Guimond N., Lecavallier M., and Fagnou K. J. Am. Chem. Soc. 131 (2009) 3291
3. Vijaya G., Zhiqin J., Akritopoulou-Zanze I., Abad-Zapatero C., Huth J.R., Song D., Hajduk P.J., Johnson E.F., Glaser K.B., Marcotte P.A., Pease L., Soni N.B., Stewart K.D., Davidsen S.K., Michaelides M.R., and Djuric S.W. Bioorg. Med. Chem. Lett. 18 (2008) 2691
4. Menichincheri M., Bargiotti A., Berthelsen J., Bertrand J.A., Bossi R., Ciavolella A., Cirla A., Cristiani C., Croci V., D'Alessio R., Fasolini M., Fiorentini F., Forte B., Isacchi A., Martina K., Molinari A., Montagnoli A., Orsini P., Orzi F., Pesenti E., Pezzetta D., Pillan A., Poggesi I., Roletto F., Scolaro A., Tato M., Tibolla M., Valsasina B., Varasi M., Volpi D., Santocanale C., and Vanotti E. J. Med. Chem. 52 (2009) 293
5. Vanotti E., Amici R., Bargiotti A., Berthelsen J., Bosotti R., Ciavolella A., Cirla A., Cristiani C., D'Alessio R., Forte B., Martina K., Menichincheri M., Molinari A., Montagnoli A., Orsini P., Pillan A., Roletto F., Scolaro A., Tibolla M., Valsasina B., Varasi M., Volpi D., and Santocanale C. J. Med. Chem. 51 (2008) 487
6. Metal Catalyzed Cross Coupling Reactions. In: Diederich F., and Stang P.J. (Eds) (1998), Wiley-VCH, New York, NY
7. Prim D., Campagne J.M., Joseph D., and Andrioletti B. Tetrahedron 58 (2002) 2041
8. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337
9. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
10. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428
11. Hassan J., Sevignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
12. Bringmann G., Walter R., and Weirich R. Angew. Chem., Int. Ed. Engl. 102 (1990) 1006
13. Hartwig J.F. Handbook of Organopalladium Chemistry for Organic Synthesis (2002), Wiley-Interscience, New York, NY p 1051, 1097
14. Yang B.H., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125
15. Lyle, F.R. U.S. Patent 5 973 257, 1985;
16. Chem. Abstr. 65 (1985) 2870
17. Nishiwaki T. Tetrahedron 22 (1966) 2401
18. Mitchell R.H., Lai Y.-Y., and Williams R.V. J. Org. Chem. 44 (1979) 4733
19. Aiello E., Dattolo G., Cirrincione G., Almerico A.M., and D'Asdia I. J. Heterocycl. Chem. 19 (1982) 977
20. Vanotti, E.; Caldarelli, M.; Cirla, A.; Forte, B.; Ermoli, A.; Menichincheri, M.; Pillan, A.; Scolaro, A. PCT Int. Appl. 2007, WO2007110344.
21. Rossignol E., Youssef A., Moreau P., Prudhomme M., and Anizon F. Tetrahedron 63 (2007) 10169
22. Examples of cross-coupling reactions on 3-halopyrroles are reported, for instance, in:
23. Bumagin N.A., Sokolova A.F., Beletskaya I.P., and Wolz G. Russ. J. Org. Chem. 29 (1993) 136
24. Banwell M.G., Flynn B.L., Hockless D.C.R., Longmore R.W., and Rae A.D. Aust. J. Chem. 52 (1999) 755
25. Liu J.H., Yang Q.-C., Mak T.C.W., and Wong H.N.C. J. Org. Chem. 65 (2000) 3587
26. Wang J., and Scott A.I. Tetrahedron Lett. 36 (1995) 7043
27. Handy S.T., Zhang Y., and Bregman H. J. Org. Chem. 69 (2004) 2362
28. Walker S.R., Carter E.J., Huff B.C., and Morris J.C. Chem. Rev. (2009) 10.1021/cr900032s
29. Merkushev E.B. Synthesis (1988) 923
30. Schröeter S., Stock C., and Bach T. Tetrahedron 61 (2005) 2245
31. Carreño M.C., Ruano J.L., Sanz G., Toledo M.A., and Urbano A. Tetrahedron Lett. 37 (1996) 4081
32. Legault C.Y., Garcia Y., Merlic C.A., and Houk K.N. J. Am. Chem. Soc. 129 (2007) 12664
33. Colombo M., Sirtori F.R., and Rizzo V. Rapid Commun. Mass Spectrom. 18 (2004) 511