A novel scalable process to the GSK3β inhibitor AZD8926 based on a heterocyclic ziegler coupling

Organic Process Research and Development

Volumn 17, Issue 4, 2013, Pages 672-678

  Witt, Anette ^a,b   Teodorovic, Peter ^a   Linderberg, Mats ^a   Johansson, Peter ^a   Minidis, Anna ^a,c  

^a ASTRAZENECA R AND D   (Sweden)

^b Cambrex Karlskoga   (Sweden)

^c SP TECHNICAL RESEARCH INSTITUTE OF SWEDEN   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BUCHWALD-HARTWIG COUPLINGS; C-N BOND FORMATIONS; HAZARDOUS PROPERTIES; PROCESS SAFETY; STOICHIOMETRIC OXIDANT;

EID: 84876583385     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op300365e     Document Type: Article

References (27)

1. Bhat, R. V.; Budd, S. L. Neurosignals 2002, 11, 251
2. Bhat, R. V.; Budd Haeberlein, S. L.; Avila, J. J. Neurochem. 2004, 89, 1313
3. Johansson, S.; Jämsä, A.; Vasänge, M.; Winblad, B.; Luthman; Cowburn, R. F. Neurochemistry 2006, 17, 907
4. Andersson, L.; Arzel, E.; Berg, S.; Burrows, J.; Hellberg, S.; Huerta, F.; Pedersen, T.; Rein, T.; Rotticci, D.; Staaf, K.; Turek, D. (Astrazeneca AB, Sweden). PCT Int. Appl. WO/2007/040440 A1, 2007.
5. Owen, D.; Plevey, R. G.; Tatlow, J. C. J. Fluorine Chem. 1981, 17, 179
6. Kimoto, H.; Fujii, S.; Cohen, L. A. J. Org. Chem. 1982, 47, 2867
7. Wiehn, M. S.; Vinogradova, E. V.; Togni, A. J. Fluorine Chem. 2010, 131, 951
8. Tamura, K.; Mizukami, H.; Maeda, K.; Watanabe, H.; Uneyama, K. J. Org. Chem. 1993, 58, 32
9. Cotarca, L.; Delogu, P.; Nardelli, A.; Šunjić, V. Synthesis 1996, 553
10. Frutos, R. P.; Rodríguez, S.; Patel, N.; Johnson, J.; Saha, A.; Krishnamurthy, D.; Senanayake, C. H. Org. Process Res. Dev. 2007, 11, 1076
11. Manley, P. J.; Balitza, A. E.; Bilodeau, M. T.; Coll, K. E.; Hartman, G. D; McFall, R. C; Rickert, K. W.; Rodman, L. D.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2003, 13, 1673
12. Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467
13. Bellina, F.; Cauteruccio, S.; Mannina, L.; Rossi, R.; Viel, S. Eur. J. Org. Chem. 2006, 693
14. Aoyagi, Y.; Inoue, A.; Koizumi, I.; Otha, A. Heterocycles 1992, 257
15. Schnürch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 3283
16. Hueter, O. F.; Brunner, H.-G.; Muehlebach, M.; O'Sullivan, A. (Syngenta Participations AG, Switzerland). PCT Int. Appl. WO/2005/047281 A1, 2005.
17. Zhong, Y.-L.; Lee, J.; Reamer, R. A.; Askin, D. Org. Lett. 2004, 6, 929
18. Dobler, M. R. Tetrahedron Lett. 2003, 44, 7115
19. Rieke, R. Aldrichimica Acta 2000, 33, 52
20. Bursavich, M. G.; Lombardi, S.; Gilbert, A. M. Org. Lett. 2005, 7, 4113
21. Shin Cho, Y.; Borland, M.; Brain, C.; Chen, C. H.-T.; Cheng, H.; Chopra, R.; Chung, K.; Groarke, J.; He, G.; Hou, Y.; Kim, S.; Kovats, S.; Lu, Y.; O'Reilly, M.; Shen, J.; Smith, T.; Trakshel, G.; Vögtle, M.; Xu, M.; Je Sung, M. J. Med. Chem. 2010, 53, 7938
22. Harden, D. B.; Mokrosz, M. J.; Strekowski, L. J. Org. Chem. 1988, 53, 4137
23. Ziegler, K.; Zeiser, H. Justus Liebigs. Ann. Chem. 1931, 174
24. Yamamoto, K.; Chen, Y. G.; Buono, F. G. Org. Lett. 2005, 7, 4673
25. Gunzenhauser, S.; Balli, H. Helv. Chim. Acta 1988, 71, 33
26. Nozaki, S. Org. Lett. 1997, 1
27. Nozaki, S. Pept. Res. 1999, 54, 162