Kilogram-lab-scale oxindole synthesis via palladium-catalyzed c-h functionalization

Organic Process Research and Development

Volumn 16, Issue 2, 2012, Pages 255-259

  Kiser, E Jason ^b   Magano, Javier ^a   Shine, Russell J ^a   Chen, Michael H ^c  

^a PFIZER INC   (United States)

^b ASH STEVENS INC   (United States)

^c Wuhan Masteam Bio Technology Research Institute   (China)

Author keywords

[No Author keywords available]

Indexed keywords

C-H FUNCTIONALIZATION; CHLOROACETANILIDES; EN-ROUTE; FIVE-MEMBERED RINGS; LABORATORY FACILITIES; SCALABLE METHODS;

AMINO ACIDS; SCALABILITY;

CATALYSIS;

EID: 84863181223     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200332p     Document Type: Article

References (18)

1. Bolton, G. L.; Hutchings, R. H.; Kohrt, J. T; Park, W. K. C.; Van Huis, C. A. WO 2008084300 A1 20080717, 2008
2. Chem. Abst. 149, 153082.
3. Hanada, K. Biochim. Biophys. Acta 2003, 1632, 16
4. deGoma, E. M.; Rader, D. J. Nat. Rev. Cardiol. 2011, 8, 266
5. Castelli, W. P.; Garrison, R. J.; Wilson, P. W.; Abbott, R. D.; Kalousdian, S.; Kannel, W. B. JAMA, J. Am. Med. Assoc. 1986, 256, 2835
6. Grundy, S. M. Am. J. Cardiol. 2002, 90, 11i
7. Johnson, D. J.; Forbes, I. T.; Watson, S. P.; Garzya, V.; Stevenson, G. I.; Walker, G. R.; Mudhar, H. S.; Flynn, S. T.; Wyman, P. A.; Smith, P. W.; Murkitt, G. S.; Lucas, A. J.; Mookherjee, C. R.; Watson, J. M.; Gartlon, J. E.; Bradford, A. M.; Brown, F. Bioorg. Med. Chem. Lett. 2010, 20, 5434
8. Zimmermann, K.; Wittman, M. D.; Saulnier, M. G.; Velaparthi, U.; Langley, D. R.; Sang, X.; Frennesson, D.; Carboni, J.; Li, A.; Greer, A.; Gottardis, M.; Attar, R. M.; Yang, Z.; Balimane, P.; Discenza, L. N.; Vyas, D. Bioorg. Med. Chem. Lett. 2008, 18, 4075
9. Zaveri, N. T.; Jiang, F.; Olsen, C. M.; Deschamps, J. R.; Parrish, D.; Polgar, W.; Toll, L. J. Med. Chem. 2004, 47, 2973
10. Forbes, I. T. Tetrahedron Lett. 2001, 42, 6943
11. Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084
12. Beckett, A. H.; Daisley, R. W.; Walker, J. Tetrahedron 1968, 24, 6093
13. Ben-Ishai, D.; Peled, N.; Sataty, I. Tetrahedron Lett. 1980, 21, 569
14. For a recent application of this method to the synthesis of an oxazolidinone antibacterial, see: Choy, A.; Colbry, N.; Huber, C.; Pamment, M.; Van Duine, J. Org. Process Res. Dev. 2008, 12, 884
15. Dwivedi, A. M. Pharm. Technol. 2002, 26, 42
16. Withbroe, G. J.; Singer, R. A.; Sieser, J. E. Org. Process Res. Dev. 2008, 12, 480
17. Singer, R. A.; Doré, M.; Sieser, J. E.; Berliner, M. A. Tetrahedron Lett. 2006, 47, 3727
18. Singer, R. A.; Caron, S.; McDermott, R. E.; Arpin, P.; Do, N. M. Synthesis 2003, 1727