Straightforward protocol for the efficient synthesis of varied N 1-acylated (aza)indole 2-/3-alkanoic acids and esters: Optimization and scale-up

Tetrahedron

Volumn 68, Issue 48, 2012, Pages 10049-10058

  Liedtke, Andy J ^a   Kim, Kwangho ^a   Stec, Donald F ^a   Sulikowski, Gary A ^a   Marnett, Lawrence J ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

(2 Des methyl) indomethacin; Heterocyles; Indoles; Microwave synthesis; Synthesis scale up

Indexed keywords

2 (1 (4 (CHLOROMETHYL)BENZOYL) 5 METHOXY 2 METHYL 1H INDOL 3 YL)ACETIC ACID; 2 (1 (4 CHLOROBENZOYL) 5 FLUORO 1H INDOL 3 YL)ACETIC ACID; 2 (1 (4 CHLOROBENZOYL) 5 METHOXY 1H INDOL 3 YL)ACETIC ACID; 2' METHYL INDOMETHACIN; 3 (1 (4 CHLOROBENZOYL) 5 METHOXY 3 METHYL 1H INDOL 2 YL) N (METHYLSULFONYL)PROPANAMIDE; 3 (1 (4 CHLOROBENZOYL) 5 METHOXY 3 METHYL 1H INDOL 2 YL)PROPANOIC ACID; 6 METHOXY 9 (3 (TRIFLUOROMETHYL)BENZOYL) 2,3,4,9 TETRAHYDRO 1H CARBAZOLE 3 CARBOXYLIC ACID; ALKANOIC ACID; ALLYL 2 (1 (4 CHLOROBENZOYL) 5 METHOXY 1H INDOL 3 YL)ACETATE; ALLYL 2 (5 METHOXY 1H INDOL 3 YL)ACETATE; ALLYL 3 (1 (4 CHLOROBENZOYL) 5 METHOXY 3 METHYL 1H INDOL 2 YL)PROPANOATE; ALLYL 3 (5 METHOXY 3 METHYL 1H INDOL 2 YL)PROPANOATE; ALLYL 4 OXOHEXANOATE; ESTER DERIVATIVE; INDOLE DERIVATIVE; INDOMETACIN; INDOMETACIN DERIVATIVE; METHYL 2 (1 (4 CHLOROBENZOYL) 1H INDAZOL 3 YL)ACETATE; METHYL 2 (1H INDAZOL 3 YL)ACETATE; METHYL 2 (5 FLUORO 1H INDOL 3 YL)ACETATE; METHYL 2 (5 METHOXY 1H PYRROLO[3,2 B]PYRIDIN 3 YL)ACETATE; METHYL 2 (5 METHOXY 2 METHYL 1 (4 METHYLBENZOYL) 1H INDOL 3 YL)ACETATE; METHYL 3 (1 (4 CHLOROBENZOYL) 5 FLUORO 2 METHYL 1H INDOL 3 YL)PROPANOATE; METHYL 3 (5 FLUORO 3 METHYL 1H INDOL 2 YL)PROPANOATE; METHYL 6 METHOXY 2,3,4,9 TETRAHYDRO 1H CARBAZOLE 3 CARBOXYLATE; METHYL 6 METHOXY 9 (3 (TRIFLUOROMETHYL)BENZOYL) 2,3,4,9 TETRAHYDRO 1H CARBAZOLE 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE RADIATION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 84867572903     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.08.044     Document Type: Article

References (41)

1. Bartolini, W.; Cali, B. M.; Chen, B.; Chien, Y. -T.; Currie, M. G.; Milne, G. T.; Pearson, J. P.; Talley, J. J.; Zimmerman, C. (USA). Application: US US, 2005, 118 pp., Cont-in-part of US Ser No 883,900.
2. Munoz, B.; Prasit, P.; Stock, N. S. (Merck & Co., Inc., USA). Application: WO WO, 2004 WO, 2004, 40 pp.
3. K. Torisu, K. Kobayashi, M. Iwahashi, H. Egashira, Y. Nakai, Y. Okada, F. Nanbu, S. Ohuchida, H. Nakai, and M. Toda Bioorg. Med. Chem. Lett. 14 2004 4557 4562
4. K. Torisu, K. Kobayashi, M. Iwahashi, H. Egashira, Y. Nakai, Y. Okada, F. Nanbu, S. Ohuchida, H. Nakai, and M. Toda Eur. J. Med. Chem. 40 2005 505 519
5. S.-J. Wey, M.E. Augustyniak, E.D. Cochran, J.L. Ellis, X. Fang, D.S. Garvey, D.R. Janero, L.G. Letts, A.M. Martino, T.L. Melim, M.G. Murty, S.K. Richardson, J.D. Schroeder, W.M. Selig, A.M. Trocha, R.S. Wexler, D.V. Young, I.S. Zemtseva, and B.M. Zifcak J. Med. Chem. 50 2007 6367 6382
6. A.L. Blobaum, and L.J. Marnett J. Med. Chem. 50 2007 1425 1441
7. K.D. Rainsford Subcell. Biochem. 42 2007 3 27
8. J.L. Wallace, W. McKnight, B.K. Reuter, and N. Vergnolle Gastroenterology 119 2000 706 714
9. D.A. Sandham, C. Adcock, K. Bala, L. Barker, Z. Brown, G. Dubois, D. Budd, B. Cox, R.A. Fairhurst, M. Furegati, C. Leblanc, J. Manini, R. Profit, J. Reilly, R. Stringer, A. Schmidt, K.L. Turner, S.J. Watson, J. Willis, G. Williams, and C. Wilson Bioorg. Med. Chem. Lett. 19 2009 4794 4798
10. A.S. Felts, C. Ji, J.B. Stafford, B.C. Crews, P.J. Kingsley, C.A. Rouzer, M.K. Washington, K. Subbaramaiah, B.S. Siegel, S.M. Young, A.J. Dannenberg, and L.J. Marnett ACS Chem. Biol. 2 2007 479 483
11. M.C. Byrns, S. Steckelbroeck, and T.M. Penning Biochem. Pharmacol. 75 2008 484 493
12. G.A. Piazza, A.B. Keeton, H.N. Tinsley, J.D. Whitt, B.D. Gary, B. Mathew, R. Singh, W.E. Grizzle, and R.C. Reynolds Pharmaceuticals 3 2010 1652 1667
13. R. Schuligoi, E. Sturm, P. Luschnig, V. Konya, S. Philipose, M. Sedej, M. Waldhoer, B.A. Peskar, and A. Heinemann Pharmacology 85 2010 372 382
14. A.N. Hata, T.P. Lybrand, L.J. Marnett, and R.M. Breyer Mol. Pharmacol. 67 2005 640 647
15. Marnett, L. J.; Prusakiewicz, J. J.; Felts, A. S.; Ji, C. (Vanderbilt University, USA). Application: US US, 2005, 63 pp.
16. J.J. Prusakiewicz, A.S. Felts, B.S. Mackenzie, and L.J. Marnett Biochemistry 43 2004 15439 15445
17. C. Mukai, and Y. Takahashi Org. Lett. 7 2005 5793 5796
18. B.E. Maki, and K.A. Scheidt Org. Lett. 11 2009 1651 1654
19. K.R. Campos, J.C.S. Woo, S. Lee, and R.D. Tillyer Org. Lett. 6 2004 79 82
20. H. Takahashi, S. Wakamatsu, H. Tabata, T. Oshitari, A. Harada, K. Inoue, and H. Natsugari Org. Lett. 13 2011 760 763
21. H. Yamamoto J. Org. Chem. 32 1967 3693 3695
22. H. Yamamoto Chem. Pharm. Bull. (Tokyo) 16 1968 17 19
23. A.R. Maguire, S.J. Plunkett, S. Papot, M. Clynes, R. O'Connor, and S. Touhey Bioorg. Med. Chem. 9 2001 745 762
24. K.C. Nicolaou, A.A. Estrada, M. Zak, S.H. Lee, and B.S. Safina Angew. Chem., Int. Ed. 44 2005 1378 1382
25. A.S. Kalgutkar, B.C. Crews, S. Saleh, D. Prudhomme, and L.J. Marnett Bioorg. Med. Chem. 13 2005 6810 6822
26. R.S.E. Conn, A.W. Douglas, S. Karady, E.G. Corley, A.V. Lovell, and I. Shinkai J. Org. Chem. 55 1990 2908 2913
27. G.R. Allen Jr. J. Heterocycl. Chem. 7 1970 239 241
28. S.V. Karthikeyan, S. Perumal, K.A. Shetty, P. Yogeeswari, and D. Sriram Bioorg. Med. Chem. Lett. 19 2009 3006 3009
29. A. Vasudevan, A.J. Souers, J.C. Freeman, M.K. Verzal, J. Gao, M.M. Mulhern, D. Wodka, J.K. Lynch, K.M. Engstrom, S.H. Wagaw, S. Brodjian, B. Dayton, D.H. Falls, E. Bush, M. Brune, R.D. Shapiro, K.C. Marsh, L.E. Hernandez, C.A. Collins, and P.R. Kym Bioorg. Med. Chem. Lett. 15 2005 5293 5297
30. M. Jeanty, F. Suzenet, and G. Guillaumet J. Org. Chem. 73 2008 7390 7393
31. Mylari, B. L.; Zembrowski, W. J. (Pfizer Inc., USA). Application: EP EP, 1989, 15 pp.
32. K. Honba, T. Yamada, M. Yoneda, Y. Ohkawa, and H. Nagai Iyakuhin Kenkyu 13 1982 323 333
33. F. Guibe Tetrahedron 54 1998 2967 3042
34. J. Tsuji, and T. Mandai Synthesis 1996 1 24
35. L.J. Goossen, and A. Doehring Synlett 2004 263 266
36. J.C. Lee, Y.S. Oh, S.H. Cho, and J. Lee II Org. Prep. Proced. Int. 28 1996 480 483
37. G.W. Anderson, and F.M. Callahan J. Am. Chem. Soc. 82 1960 3359 3363
38. H. Kunz, and H. Waldmann Helv. Chim. Acta 68 1985 618 622
39. Y. Choi, H. Ishikawa, J. Velcicky, G.I. Elliott, M.M. Miller, and D.L. Boger Org. Lett. 7 2005 4539 4542
40. A.O. Adeniji, B.M. Twenter, M.C. Byrns, Y. Jin, M. Chen, J.D. Winkler, and T.M. Penning J. Med. Chem. 55 2012 2311 2323
41. Mylari, B. L.; Zembrowski, W. J. (Pfizer Inc., USA). Application: US US, 1993, p 8, Cont of US Ser No 499,279, abandoned.