The synthesis of a novel inhibitor of B-Raf kinase

Organic Process Research and Development

Volumn 10, Issue 1, 2006, Pages 70-77

  Denni Dischert, Donatienne ^a   Marterer, Wolfgang ^a   Bänziger, Markus ^a   Yusuff, Naeem ^b   Batt, David ^b   Ramsey, Tim ^b   Geng, Peng ^b   Michael, Walter ^b   Wang, Run Ming B ^b   Taplin Jr , Francis ^b   Versace, Richard ^b   Cesarz, David ^b   Perez, Lawrence B ^b  

^a NOVARTIS PHARMA AG   (Switzerland)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33344471044     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0501601     Document Type: Article

References (19)

1. Smith, J. K.; Mamoon, N. M.; Duhe, R. J. Oncol. Res. 2003, 14(4,5), 175.
2. Deininger, M.; Buchdunger, E.; Druker, B. J. Blood 2005, 105(7), 2640.
3. Sridhar, S. S.; Hedley, D.; Siu, L. L. Mol. Cancer Ther. 2004, 4(4), 677.
4. Davies, H.; Bignell, G. R.; Cox, C.; Stephens, P.; Edkins, S.; Clegg, S.; Teague, J.; Woffendin, H.; Garnett, M. J.; Bottomley, W.; Davis, N.; Dicks, E.; Ewing, R.; Floyd, Y.; Gray, K.; Hall, S.; Hawes, R.; Hughes, J.; Kosmidou, V.; Menzies, A.; Mould, C.; Parker, A.; Stevens, C.; Watt, S.; Hooper, S.; Wilson, R.; Jayatilake, H.; Gusterson, B. A.; Cooper, C.; Shipley, J.; Hargrave, D.; Pritchard-Jones, K.; Maitland, N.; Chenevix-Trench, G.; Riggins, G. J.; Bigner, D. D.; Palmieri, G.; Cossu, A.; Flanagan, A.; Nicholson, A.; Ho, J. W. C.; Leung, S. Y.; Yuen, S. T.; Weber, B. L.; Seigler, H. F.; Darrow, T. L.; Paterson, H.; Marais, R.; Marshall, C. J.; Wooster, R.; Stratton, M. R.; Futreal, P. A. Nature 2002, 417(6892), 949.
5. Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42(10), 1821.
6. Baston, E.; Hartmann, R. W. Synth. Commun. 1998, 28(14), 2725.
7. Hirao, K.; Tsuchiya, R.; Yano, Y.; Tsue, H. Heterocycles 1996, 42(1), 415;
8. Briet, N.; Brookes, M. H.; Davenport, R. J.; Galvin, F. C. A.; Gilbert, P. J.; Mack, S. R.; Sabin, V. Tetrahedron 2002, 58(29), 5761.
9. (a) Szulc, Z.; Fikus, M.; Mlochowski, J.; Palus, J. Monatsh. Chem. 1988, 119(3), 263.
10. (b) Brown, E. V.; Plasz, A. C. J. Heterocycl. Chem. 1971, 8(2), 303.
11. Prudent Practices in the Laboratory; National Academy Press: Washington, D.C., 1995.
12. Arnold, Z.; Sauliova, J.; Krchnak, V. Collect. Czech. Chem. Commun. 1973, 38(9), 2633.
13. (a) Krchnak, V.; Arnold, Z. Collect. Czech. Chem. Commun. 1975, 40(5), 1384.
14. (b) Ohta, K.; Kawachi, E.; Inoue, N.; Fukasawa, H.; Hashimoto, Y.; Itai, A.; Kagechika, H. Chem. Pharm. Bull. 2000, 48(10), 1504.
15. Prashad, M.; Hu, B.; Har, D.; Repic, O.; Blacklock, T. J.; Acemoglu, M. Adv. Synth. Catal. 2001, 343(5), 461-472.
16. Prashad, M.; Hu, B.; Lu, Y.; Draper, R.; Har, D.; Repic, O.; Blacklock, T. J. J. Org. Chem. 2000, 65(8), 2612.
17. Manley, P. W.; Acemoglu, M.; Marterer, W.; Pachinger, W. Org. Process Res. Dev. 2003, 7, 436.
18. 4" lot whose brilliant orange color indicated some air-oxidation and that according to elemental analysis contained one equivalent of triphenylphosphine oxide. This crystalline form, however, is no longer commercially available. Other more stable Pd- or Ni catalysts and ligands known to be useful for the Negishi coupling were not tested at this stage of development.
19. Prashad, M.; Liu, Y.; Repic, O. Adv. Synth. Catal. 2003, 345(4), 533.