Asymmetric synthesis of a glucagon receptor antagonist via friedel-crafts alkylation of indole with chiral α-phenyl benzyl cation

Organic Process Research and Development

Volumn 16, Issue 11, 2012, Pages 1832-1845

  Chung, John Y L ^a   Steinhuebel, Dietrich ^a   Krska, Shane W ^a   Hartner, Fred W ^a   Cai, Chaoxian ^a   Rosen, Jonathan ^a   Mancheno, Danny E ^a   Pei, Tao ^a   Dimichele, Lisa ^a   Ball, Richard G ^a   Chen, Cheng Yi ^a   Tan, Lushi ^a   Alorati, Antony D ^b   Brewer, Sarah E ^b   Scott, Jeremy P ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; ARYLATIONS; ASYMMETRIC HYDROGENATION; ASYMMETRIC SYNTHESIS; BENZYL CATIONS; CONVERGENT SYNTHESIS; DRUG CANDIDATES; DRUG SUBSTANCES; DYNAMIC KINETIC RESOLUTION; EFFICIENT SYNTHESIS; FRIEDEL-CRAFTS ALKYLATION; RECEPTOR ANTAGONISTS; STEREOGENIC CENTERS; TYPE-2 DIABETES;

ETHANE; HYDROGENATION; KETONES; POSITIVE IONS;

ALKYLATION;

EID: 84869444503     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op300249q     Document Type: Article

References (44)

1. Zimmet, P.; Albert, K. G. M. M.; Shaw, J. Nature 2001, 414, 782-787
2. Adeghate, E.; Schattner, P.; Dunn, E. Ann. N. Y. Acad. Sci. 2006, 1084, 1-29
3. Adeghate, E.; Kalasz, H.; Veress, G.; Tekes, K. Curr. Med. Chem. 2010, 17, 517-551
4. Drucker, D.; Easley, D.; Kirkpatrick, P. Nat. Rev. Drug Discovery 2007, 6, 109-110
5. Doupis, J.; Veves, A. Adv. Ther. 2008, 25, 627-643
6. Stelmach, J. E.; Parmee, E. R.; Tata, J. R.; Rosauer, K. G.; Kim, R. M.; Bittner, A. R.; Chang, J.; Sinz, C. J. PCT Int. Appl. (2008), WO 2008042223, CAN148:449451.
7. Stelmach, J. E.; Parmee, E. R.; Tata, J. R.; Rosauer, K. G.; Kim, R. M.; Bittner, A. R.; Chang, J.; Sinz, C. J. U.S. patent (2010), 7687534, CAN152:381190.
8. Stelmach, J.; Rosauer, K.; Bansal, A.; Brady, E.; Candelore, M.; Dallas-Yang, Q.; Jiang, G.; Miller, C.; Qureshi, S.; Salituro, G.; Shang, J.; Tota, L.; Wright, M.; Yang, X.; Xu, L.; Xu, S.; Hammond, M.; Tata, J.; Zhang, B.; Parmee, E. R. Highly Potent Indole Derived Glucagon Receptor Antagonists for the Treatment of Type 2 Diabetes. Presented at the 33rd National Medicinal Chemistry Symposium, Tuscon, AZ, May 20-23, 2012; Poster 105.
9. Chung, J. Y. L.; Mancheno, D.; Dormer, P. G.; Variankaval, N.; Ball, R. G.; Tsou, N. N. Org. Lett. 2008, 10, 3037-3040
10. Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130
11. Mühlthau, F.; Schuster, O.; Bach, T. J. Am. Chem. Soc. 2005, 127, 9348-9349
12. Mühlthau, F.; Stadler, D.; Goeppert, A.; Olah, G. A.; Prakash, G. K. S.; Bach, T. J. Am. Chem. Soc. 2006, 128, 9668-9675
13. Stadler, D.; Mühlthau, F.; Rubenbauer, P.; Herdtweck, E.; Bach, T. Synlett 2006, 2573-2576
14. Ward, R. S. Tetrahedron 1995, 6, 1475-1490
15. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T; Noyori, R. J. Org. Chem. 1996, 61, 4872-4873
16. Chen, C.-Y.; Frey, L. F.; Shultz, S.; Wallace, D. J.; Marcantonio, K.; Payack, J. F.; Vazquez, E.; Springfield, S. A.; Zhou, G.; Liu, P.; Kieczykowski, G. R.; Chen, A.; Phenix, B. D.; Singh, U.; Strine, J.; Izzo, B.; Krska, S. W. Org. Process Res. Dev. 2007, 11, 616-623
17. Shultz, C. S.; Krska, S. W. Acc. Chem. Res. 2007, 40, 1320-1326
18. Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109
19. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478
20. Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370
21. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519
22. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096
23. Gillespie, R. J.; Lerpiniere, J.; Gaur, S.; Bamford, S. J.; Stratton, G. C.; Leonardi, S.; Weiss, S. M. PCT Int. Appl. (2002), WO 2002055083.
24. Dalpozzo, R.; Bartoli, G. Curr. Org. Chem. 2005, 9, 163-178
25. Yonekubo, S.; Fushimi, N. EP 1813611 (2007).
26. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689
27. Shen, M.; Li, G.; Lu, B. Z.; Hossain, A.; Roschangar, F.; Farina, V.; Senanayake, C. H. Org. Lett. 2004, 6, 4129-4132
28. Kristensen, J. L. Tetrahedron Lett. 2008, 49, 2351-2354
29. Blears, D. J.; Danyluk, S. S.; Schaeffe, T. J. Chem. Phys. 1967, 47, 5037
30. http://www.crhf.org.uk/incident09.html. "A spontaneous and strongly exothermic interaction occurs between bromine and tert -butyl methyl ether at a molar ratio of approximately 1:1, resulting in uncontrolled and violent pressurization due to the rapid vaporization of the solvent. The calculated heat of reaction was in excess of -350 kJ/litre and the associated adiabatic temperature rise was greater than 150 °C."
31. As far as we are aware of, the use of terminal alkyne TMS-acetylene with unprotected 2-bromoaniline in the Larock indole synthesis is unprecedented prior to our disclosure in 2010: Chung, J. Y. L.; Zhang, Y.; Artino, L.; Baxter, J.; Cote, A. S.; Desmond, D.; Scott, J.; Vaynshteyn, Y. PCT Int. Appl. (2010), WO 2010080971, CAN153:204191.
32. For a general review regarding Pd-catalyzed annulations of alkynes, see: Larock, R. C. Top. Organomet. Chem. 2005, 14, 147-182
33. Rao, R. M.; Reddy, C. H.; Alinakhi, U.; Mulakayala, N.; Alvala, M.; Arunasree, M. K.; Poondra, R. R.; Iqbal, J.; Pal, M. Org. Biomol. Chem. 2011, 9, 3808-3816
34. Gavara, L.; Anizon, F.; Moreau, P. Tetrahedron 2011, 67, 7330-7335
35. Faeh, C.; Kuehne, H.; Luebbers, T.; Mattei, P.; Maugeais, C.; Pflieger, P. Patent: US2007/185113 A1, 2007.
36. Otabashi, M.; Giacomelli, F.; Lemaire, C.; Plenevaux, A.; Luxen, A. J. Label. Compd. Radiopharm. 2003, 46, S223-S223
37. Sugasawa, T.; Adachi, M.; Sasakura, K.; Kitagawa, A. J. Org. Chem. 1979, 44, 578-586
38. Pei, T.; Chen, C.-Y.; Dormer, P. G.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 120, 4299-4301
39. Pei, T.; Tellers, D. M.; Streckfuss, E. C.; Chen, C.-Y.; Davies, I. W. Tetrahedron 2009, 65, 3285-3281
40. Quartarone, G.; Ronchin, L.; Tortato, C.; Vavasori, A. Int. J. Chem. Kinet. 2008, 41, 107-112 and references therein.
41. Li., B.; Berliner, M.; Buzon, R.; Chiu, C. K.-F.; Colgan, S. T.; Kaneko, T.; Keene, N.; Kissel, W.; Le, T.; Leeman, K. R.; Marquez, B.; Morris, R.; Newell, L.; Wunderwald, S.; Witt, M.; Weaver, J.; Zhang, S.; Zhang, Z. J. Org. Chem. 2006, 71, 9045-9050
42. Molnar, A. Curr. Org. Chem. 2011, 15, 3928-3960
43. Amandi, R.; Licence, P.; Ross, S. K.; Aaltonen, O.; Poliakoff, M. Org. Process Res. Dev. 2005, 9, 451-456 and references therein.
44. Shirakawa, S.; Kobayashi, S. Org. Lett. 2007, 9, 311-314