Solution-Phase Synthesis of an Aminomethyl-Substituted Biaryl Library via Sequential Amine N-Alkylation and Suzuki Cross-Coupling

Journal of Combinatorial Chemistry

Volumn 3, Issue 5, 2001, Pages 473-476

  Organ, Michael G ^a   Arvanitis, Elena A ^a   Dixon, Craig E ^a   Lavorato, David J ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN RECEPTOR; BORONIC ACID DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LOSARTAN;

ALKYLATION; ARTICLE; CHEMISTRY; DRUG ANTAGONISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ALKYLATION; BORONIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDICATORS AND REAGENTS; LOSARTAN; MAGNETIC RESONANCE SPECTROSCOPY; RECEPTORS, ANGIOTENSIN;

EID: 0035461111     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc010018l     Document Type: Article

References (23)

1. For discussion of the "olefin template strategy" for efficient olefin synthesis, see the following. (a) Organ M. G.; Cooper, J. T.; Rogers, L. R.; Soleymanzadeh, F.; Paul, T. J. Org. Chem. 2000, 65, 7959-7970. (b) Organ, M. G.; Bratovanov, S. Tetrahedron Lett. 2000, 41, 6945-6949.
2. For discussion of the "olefin template strategy" for efficient olefin synthesis, see the following. (a) Organ M. G.; Cooper, J. T.; Rogers, L. R.; Soleymanzadeh, F.; Paul, T. J. Org. Chem. 2000, 65, 7959-7970. (b) Organ, M. G.; Bratovanov, S. Tetrahedron Lett. 2000, 41, 6945-6949.
3. Organ, M. G.; Mayhew, D.; Cooper, J. T.; Dixon, C. E.; Lavorato, D. J.; Kaldor, S. W.; Siegel, M. G. J. Comb. Chem. 2001, 3, 64-67.
4. Organ, M. G.; Kaldor, S. W.; Dixon, C. E.; Parks, D. J.; Singh, U.; Lavorato, D. J.; Isbester, P. K.; Siegel, M. G. Tetrahedron Lett. 2000, 41, 8407-8411.
5. Larsen, R. D.; King, A. O.; Chen, C. Y.; Corley, E. G.; Foster, B. S.; Roberts, F. E.; Yang, C.; Lieberman, D. R.; Reamer, R. A.; Tschaen, D. M.; Verhoeven, T. R.; Reider, P. J.; Lo, Y. S.; Rossano, L. T.; Brookes, A. S.; Meloni, D.; Moore, J. R.; Arnett, J. F. J. Org. Chem. 1994, 59, 6391-6394.
6. Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. Bioorg. Med. Chem. 1998, 6, 15-30.
7. Thurkauf, A.; Yuan, J.; Chen, X.; Wasley, J. W. F.; Paneitz, G.; Meade, R.; Woodruff, K. H.; Huston, K.; Ross, P. C. Med. Chem. Res. 1996, 6, 69-80.
8. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
9. (a) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
10. (b) Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197-1200.
11. (a) Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
12. (b) Wright, S. W.; Hageman, D. L.; McLure, L. D. J. Org. Chem. 1994, 59, 6095-6097.
13. (a) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965-967.
14. (b) Uenishi, J.; Beau, J. M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756-4758.
15. (a) Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell, J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357-3360.
16. (b) Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567-2573.
17. (c) Lawrence, R. M.; Biller, S. A.; Fryszman, O. M.; Poss, M. A. Synthesis 1997, 553-558.
18. (d) Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S. Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874-4881.
19. Organ, M. G.; Dixon, C. E. Biotechnol. Bioeng. 2000, 71, 71-77.
20. Xu, W.; Mohan, R.; Morrissey, M. M. Tetrahedron Lett. 1997, 38, 7337-7340.
21. Strong Cation eXchange sulfonic acid residues immobilized on silica gel.
22. Coulson, D. Inorg. Synth. 1972, 13, 121-124.
23. Hydromatrix-filled cartridges that facilitate the liquid/liquid extraction process: the highly hydrophilic and porous material readily absorbs small quantities of water present in the reaction mixture.