Synthesis of tetracyclic heterocompounds as selective estrogen receptor modulators. Part 1. Process development for scale-up of 2,5,8-substituted 5,11 -dihydrochromeno[4,3-c]chromene derivatives

Organic Process Research and Development

Volumn 11, Issue 3, 2007, Pages 414-421

  Li, Xun ^a,b   Reuman, Michael ^a,b   Russell, Ronald K ^a,b   Adams, Richard ^a,b   Ma, Robert ^a,b   Beish, Sandra ^a,b   Branum, Shawn ^a,b   Youells, Scott ^a,b   Roberts, Jerry ^a,b   Jain, Nareshkumar ^a,c   Kanojia, Ramesh ^a,c   Sui, Zhihua ^a,c  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

^b High Output Synthesis Department

^c Reproductive Therapeutics Department

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547911932     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op700020f     Document Type: Article

References (18)

1. (a) Chen, N.; Jain, N.; Xu, J.; Reuman, M.; Li, X.; Russell, R. K.; Sui, Z. Tetrahedron Lett. 2006, 47, 5909.
2. (b) Jain, N.; Xu, J.; Sui, Z. WO2006055694, 2006.
3. (c) Jain, N.; Kanojia, R. M.; Xu, J.; Gou, J.-Z.; Pacia, E.; Lai, M.-T.; Du, F.; Musto, A.; Allan, G.; Hahn, D.; Lundeen, S.; Sui, Z. J. Med. Chem. 2006, 49, 3056.
4. Kanojia, R. M.; Jain, N.; Xu, J.; Sui, Z. Tetrahedron Lett. 2004, 45, 5837.
5. Kanojia, R. M.; Jain, N.; Ng, R.; Sui, Z.; Xu, J. WO2003053977, 2003.
6. McKillop, A.; Swann, B. P.; Taylor, E. C. J. Am. Chem. Soc. 1973, 95, 3340.
7. King, F. E.; Neill, K. G. J. Chem. Soc. 1952, 4752.
8. Alberola, A.; Onega, A. G.; Pedrosa, R.; Bragado, J. L. P.; Amo, J. F. R. J. Heterocycl. Chem. 1983, 20, 715.
9. Cook, C. E.; Corley, R. C.; Wall, M. E. J. Org. Chem. 1965, 30, 4114.
10. Cook, C. E.; Twine, C. E., Jr. J. Chem. Soc., Chem. Commun. 1968, 791.
11. Grese, T. A.; Pennington, L. D. Tetrahedron Lett. 1995, 36, 8913.
12. Prat, D.; Benedetti, F.; Girard, G. F.; Bouda, L. N.; Larkin, J.; Wehrey, C.; Lenay, J. Org. Process Res. Dev. 2004, 8, 219.
13. Li, X.; Jain, N.; Russell, R. K.; Ma, R.; Branum, S.; Xu, J.; Sui, Z. Org. Process Res. Dev. 2006, 10, 354.
14. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
15. Harder, S.; Boersma, J.; Brandsma, L.; Kanters, J. A.; Duisenbery, A. J. M.; van Lenthe, J. H. Organametallics 1990, 9, 511.
16. Vickery, E. H.; Fahler, L. F.; Eisenbraun, E. J. J. Org. Chem. 1979, 44, 4444.
17. MacKenzie, A. R.; Moody, C. J.; Rees, C. W. Tetrahedron 1986, 42, 3259.
18. Kendall, P. M.; Johnson, J. V.; Cook, C. E. J. Org. Chem. 1979, 44, 1421.