Synthesis of indatraline using a Suzuki cross-coupling reaction and a chemoselective hydrogenation: A versatile approach

Synlett

Volumn , Issue 10, 2003, Pages 1515-1517

  Cossy, Janine ^a   Belotti, Damien ^a   Maguer, Aude ^a  

^a CNRS   (France)

Author keywords

Hydrogenation; Indanone; Indatraline; Suzuki reaction; Wilkinson's catalyst

Indexed keywords

INDANONE DERIVATIVE; INDATRALINE;

ARTICLE; CATALYST; CHEMICAL REACTION; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; STEREOCHEMISTRY; SUZUKI REACTION;

EID: 0042069794     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40868     Document Type: Article

References (25)

1. Topp, L.; Hando, J.; Dillon, P.; Roche, A.; Solowij, N. Drug Alcohol Dependence 1999, 55, 105.
2. Crome, H. B. Drug Alcohol Dependence 1999, 55, 247.
3. Yui, K.; Goto, K.; Ikemoto, D.; Ishigoro, T. Drug Alcohol Dependence 2000, 58, 67.
4. Hoffman, J. A.; Klein, H.; Eber, M.; Crosby, H. Drug Alcohol Dependence 2000, 58, 227.
5. Sorensen, J. L.; Copeland, A. L. Drug Alcohol Dependence 2000, 59, 17.
6. Baumann, M. H.; Char, G. U.; deCosta, B. R.; Rice, K. C.; Rothman, R. B. J. Pharmacol. Exp. Ther. 1994, 271, 1216.
7. Villemagne, V.; Rothman, R. B.; Yokoi, F.; Rice, K. C.; Matecka, D.; Clough, D. J.; Dannals, R. F. Synapse 1999, 32, 44.
8. (a) Gu, X. H.; Yu, H.; Jacobson, A. E.; Rothman, R. B.; Dersch, C. M.; George, C.; Flippen-Anderson, J. L.; Rice, K. C. J. Med. Chem. 2000, 43, 4868.
9. (b) Froimowitz, M.; Wu, K.-M.; Moussa, A.; Haidar, R. M.; Jurayj, J.; George, C.; Gardner, E. L. J. Med. Chem. 2000, 43, 4981.
10. Bogeso, K. P.; Christensen, A. V.; Hyttel, J.; Liljefors, T. J. Med. Chem. 1985, 28, 1817.
11. Hyttel, J.; Larsen, J. J. J. Neurochem. 1985, 44, 1615.
12. Negus, S. S.; Brandt, M. R.; Mello, N. K. J. Pharmacol. Exp. Ther. 1999, 291, 60.
13. Rosenzweig-Lipson, S.; Bergman, J.; Spealman, R. D.; Madras, B. K. Psychopharmacology 1992, 107, 186.
14. Davies, H. M. L.; Gregg, T. M. Tetrahedron Lett. 2002, 43, 4951.
15. 3-Arylindan-1-ones have been synthesized from 3-bromo-indenone and pinacol boronate esters, which have to be prepared from the corresponding boronic acids: Clark, W. M.; Kassick, A. J.; Plotkin, M. A.; Eldridge, A. M.; Lantos, I. Org. Lett. 1999, 1, 1839.
16. Heffner, R. J.; Joullié, M. Synth. Commun. 1991, 21, 2231.
17. The reaction was performed on 5-10g of indanone.
18. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
19. +], 239 (100), 211 (28), 176 (73).
20. Rylander, P. N. Catalytic Hydrogenation in Organic Syntheses; Academic Press: New York, 1979, 114.
21. Jourdant, A.; Gonzalez-Zamora, E.; Zhu, J. J. Org. Chem. 2002, 67, 3163.
22. +], 241 (77), 212 (25), 178 (60).
23. Separated by flash chromatography on silica gel (70/30 petroleum ether/EtOAc).
24. +], 197 (30), 183 (28).
25. +], 204 (30), 190 (22).