A new and direct approach to functionalized biaryl α-ketophosphonic acids via aqueous Suzuki coupling on solid support

Tetrahedron Letters

Volumn 47, Issue 1, 2006, Pages 19-22

  Li, Xianfeng ^a,b   Szardenings, Anna Katrin ^a   Holmes, Christopher P ^a   Wang, Liang ^a   Bhandari, Ashok ^a   Shi, Lihong ^a   Navre, Marc ^a   Jang, Larry ^a   Grove, J Russell ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

^b Galileo Laboratories Inc   (United States)

Author keywords

Ketophosphonic acids; Aqueous Suzuki coupling; Biaryl scaffolds; PTP inhibitors

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

AQUEOUS SOLUTION; ARBUZOV REACTION; ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICROWAVE IRRADIATION; SOLID; SUZUKI REACTION;

EID: 28544439281     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.122     Document Type: Article

References (42)

1. R. Kluger, and D.C. Pike J. Am. Chem. Soc. 99 1977 4504
2. T.A. O'Brien, R. Kluger, D.C. Pike, and R.B. Gennis Biochim. Biophys. Acta 613 1980 10
3. M. Tao, R. Bihovsky, G.J. Wells, and J.P. Mallamo J. Med. Chem. 41 1998 3912
4. J.M. Van Gelder, E. Breuer, A. Ornoy, A. Schlossman, N. Patlas, and G. Golomb Bone 16 1995 511
5. T.S. Widlanski, J.K. Myers, B. Stec, K.M. Holtz, and E.R. Kantrowitz Chem. Biol. 4 1997 489
6. M. Sekine, M. Satoh, H. Yamagata, and T. Hata J. Org. Chem. 45 1980 4162
7. A. Kume, M. Fujii, M. Sekine, and T. Hata J. Org. Chem. 49 1984 2139
8. R. Kluger, and J. Chin J. Am. Chem. Soc. 100 1978 7382
9. R. Kluger, D. Pike, and J. Chin Can. J. Chem. 56 1978 1792
10. E. Breuer, M. Safadi, M. Chorev, and D. Gibson J. Org. Chem. 55 1990 6147
11. R. Karaman, A. Goldblum, E. Breuer, and H. Lead J. Chem. Soc., Perkin Trans. 1 1989 765
12. K.S. Narayanan, and K.D. Berlin J. Am. Chem. Soc. 101 1979 109
13. K.D. Berlin, and H.A. Taylor J. Am. Chem. Soc. 86 1964 3862
14. D. Solas, R.L. Hale, and D.V. Patel J. Org. Chem. 61 1996 1537
15. A.K. Bhattacharya, and G. Thyagarajan Chem. Rev. 81 1981 415
16. T.R. Burke Jr., M.S. Smyth, M. Nomizu, A. Otaka, and P.P. Roller J. Org. Chem. 58 1993 1336
17. B. Kaboudin Tetrahedron Lett. 41 2000 3169
18. Y. Liao, H. Shabany, and C.D. Spilling Tetrahedron Lett. 39 1998 8389
19. X. Li, A. Bhandari, C.P. Holmes, and A.K. Szardenings Bioorg. Med. Chem. Lett. 14 2004 4301
20. C.P. Holmes, X. Li, Y. Pan, C. Xu, A. Bhandari, C. Moody, J. Miguel, S.W. Ferla, M.N. Defrancisco, B.T. Frederick, S. Zhou, N. Macher, L. Jang, J.D. Irvine, and J.R. Grove Bioorg. Med. Chem. Lett. 15 2005 4336
21. For recent reviews on PTP inhibitors, see Z.-Y. Zhang Annu. Rev. Pharmacol. Toxicol. 42 2002 209
22. T.O. Johnson, J. Ermolieff, and M.R. Jirousek Nat. Rev. Drug Disc. 1 2002 696
23. S.D. Taylor Curr. Top. Med. Chem. 3 2003 759
24. G. Liu Curr. Med. Chem. 10 2003 1407
25. R. Hooft van Huijsduijnen, W.H. Sauer, A. Bombrun, and D. Swinnen J. Med. Chem. 47 2004 4142
26. S.D. Taylor, C.C. Kotoris, A.N. Dinaut, Q. Wang, C. Ramachandran, and Z. Huang Bioorg. Med. Chem. 6 1998 1457
27. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
28. +-1, 100%).
29. C.G. Blettner, W.A. Konig, W. Stenzel, and T. Schotten J. Org. Chem. 64 1999 3885
30. N.E. Leadbeater, and M. Marco Org. Lett. 4 2002 2973
31. M. Larhed, C. Moberg, and A. Hallberg Acc. Chem. Res. 35 2002 717
32. B. Wathey, J. Tierney, P. Lidstrom, and J. Westman Drug Discovery Today 7 2002 373
33. A. Lee, L. Huang, and J.A. Ellman J. Am. Chem. Soc. 121 1999 9907
34. Z.H. Xu, C.R. McArthur, and C.C. Leznoff Can. J. Chem. 61 1983 1405
35. D.A. Campbell, and J.C. Bermak J. Am. Chem. Soc. 116 1994 6039
36. D.A. Campbell, and J.C. Bermak J. Org. Chem. 59 1994 658
37. G. Hum, J. Grzyb, and S.D. Taylor J. Comb. Chem. 2 2000 234
38. S.R. Piettre, and S. Baltzer Tetrahetron Lett. 38 1997 1197
39. K.J. Jensen, J. Alsina, M.F. Songster, J. Vagner, F. Albericio, and G. Barany J. Am. Chem. Soc. 120 1998 5441
40. J. Alsina, K.J. Jensen, F. Albericio, and G. Barany Chem. Eur. J. 5 1999 2787
41. 2.
42. 18 reverse phase column. The following mobile phase gradient system was used: (solvent A: water with 0.1% TFA; solvent B: acetonitrile with 0.1% TFA): 0 min, 100% A; 5 min, 100% A; 20 min, 100% B; 28 min, 100% B; 30 min, 100% A. Flow rate 12 mL/min. The yields for all the compounds were not optimized. The low yields observed are probably due to poor recovery of these highly polar compounds during HPLC purification.