Discovery of the decarboxylative biaise reaction and its application to the efficient synthesis of ethyl 2,6-dichloro-5-fluoronicotinoylacetate

Organic Process Research and Development

Volumn 11, Issue 6, 2007, Pages 1062-1064

  Lee, Jae Hoon ^a   Choi, Bo Seung ^a   Chang, Jay Hyok ^a   Kim, Sam Sik ^a   Shin, Hyunik ^a  

^a LG Chemical Ltd   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049004178     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op7001694     Document Type: Article

References (19)

1. The content of the paper has been published as a part of patent. See: Shin, H.; Choi, B. S.; Lee, J. H. WO 2007064077, 2007.
2. (a) Miyamoto, T.; Egawa, H.; Shibamori, K.; Matsumoto, J.-I. J. Heterocycl. Chem. 1987, 24, 1333-1339.
3. (b) Matsumoto, J.-I.; Miyamoto, T.; Minamida, A.; Nishimura, Y.; Egawa, H.; Nishimura, H. J. Heterocyd. Chem. 1984, 21, 673.
4. Chu, D. T. W.; Fernandes, P. B.; Claiborne, A. K.; Gracey, E. H.; Pernet, A. G. J. Med. Chem. 1986, 29, 2363.
5. (a) Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097.
6. (b) Braish, T. F.; Castaldi, M. J.; Chan, S.; Fox, D. E.; Keltonic, T.; McGarry, J.; Hawkins, J. M.; Norris, T.; Rose, P. R.; Sieser, J. E.; Sitter, B. J.; Watson, H., Jr. Synlett 1996, 1100.
7. Hong, C. Y.; Kim, Y. K.; Chang, J. H.; Kim, S. H.; Choi, H.; Nam, D. H.; Kim, Y. Z.; Kwak, J. H. J. Med. Chem. 1997, 40, 3584.
8. (a) The reported yield of 1 from the acid chloride 2 is 74%. See: Bouzard, D.; Di Cesare, P.; Essiz, M.; Jacquet, J. P.; Ledoussal, B.; Remuzon, P.; Kessler, R. E.; Fung-Tomc, J. J. Med. Chem. 1992, 35, 518.
9. (b) Miyamoto, T.; Matsumoto, J.-I. Chem. Pharm. Bull. 1990, 38, 3211.
10. 1H NMR data of the methyl ketone impurity: (300 MHz) δ 7.57 (d, J = 7.3Hz, 1H), 2.71 (s, 3H).
11. (a) The reported yield of 1 from the acid chloride 2 is 96%. Refer to ref 2.
12. (b) O'Neill, B. T.; Busch, F. R.; Lehner, R. S. EP 449445, 1991.
13. (c) Clay, R. J.; Collom, T. A.; Karrick, G. L.; Wemple, J. Synthesis 1993, 290.
14. The reported yield of 1 from the acid chloride 2 is 70%. See: Urban, F. J.; Moore, B. S.; Spargo, P. L. Org. Prep. Proced. Int. 1997, 29, 231.
15. Shin, H.; Choi, B. S.; Lee, K. K.; Choi, H.-w.; Chang, J. H.; Lee, K. W.; Nam, D. H.; Kim, N.-S. Synthesis 2004, 2629.
16. (b) Choi, B. S.; Chang, J. H.; Choi, H.-w.; Kim, Y. K.; Lee, K. K.; Lee, K. W.; Lee, J. H.; Heo, T.; Nam, D. H.; Shin, H. Org. Process Res. Dev. 2005, 9, 311.
17. Toussaint, O.; Capdevielle, P.; Maumy, M. Synthesis 1986, 1029.
18. (b) Darensbourg, D. J.; Holtcamp, M. W.; Khandelwal, B.; Reibenspies, J. H. Inorg. Chem. 1994, 33, 531.
19. 2 without any pressure build-up when a mixture of 100 kg of 4, zinc chloride, and potassium ethyl malonate is heated at reflux.