An Efficient C-H arylation of a 5-Phenyl-1 H -tetrazole derivative: A practical synthesis of an angiotensin II receptor blocker

Synthesis (Germany)

Volumn 44, Issue 20, 2012, Pages 3231-3237

  Seki, Masahiko ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

C H activation; drug synthesis; green chemistry; protecting groups; ruthenium

Indexed keywords

ANGIOTENSIN II; BIPHENYL DERIVATIVES; C-H ACTIVATION; C-H ARYLATION; CANDESARTAN; GREEN CHEMISTRY; P-CYMENE; PROTECTING GROUP; TETRAZOLE DERIVATIVES; TRANSFER HYDROGENATIONS; TRIPHENYL PHOSPHINES;

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; RUTHENIUM; RUTHENIUM COMPOUNDS;

REACTION KINETICS;

5 PHENYL 1H TETRAZOLE DERIVATIVE; CANDESARTAN HEXETIL; CARBON; PALLADIUM; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION;

EID: 84867328874     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1317131     Document Type: Article

References (49)

1. The Art of Process Chemistry. Yasuda N. Wiley-VCH Weinheim: 2011
2. Anderson N. G. Practical Process Research & Development. Academic Press Oxford: 2000
3. Green Chemistry in the Pharmaceutical Industry. Dunn P., Wells A., Williams M. T. Wiley-VCH Weinheim: 2010
4. Daugulis O., Do J.-Q, Shabashov D. Acc. Chem. Res.: 2009; 42 1074
5. Chen X., Engle K. M., Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed.: 2009; 48 5094
6. Ackermann L., Vicente R., Kapdi A. R. Angew. Chem. Int. Ed.: 2009; 48 9792
7. Willis M. C. Chem. Rev.: 2010; 110 725
8. Mkhalid I. A. I, Barnard J. H., Marder T. B., Murphy J. M., Hartwig J. F. Chem. Rev.: 2010; 110 890
9. Ackermann L. Chem. Commun.: 2010; 46 4866
10. Lyons T. W., Sanford M. S. Chem. Rev.: 2010; 110 1147
11. Ackermann L. Chem. Rev.: 2011; 111 1315
12. Neufeldt S. R., Sanford M. S. Acc. Chem. Res.: 2012; 45 936
13. Ru-catalyzed C-H activation: Oi S., Fukita S., Hirata N., Watanuki N. Miyano S, Inoue Y. Org. Lett.: 2001; 3 2579
14. See also: Ackermann L., Althammer A., Born R. Synlett: 2007; 2833
15. See also: Ackermann L. A., Althammer A. R., Born R. Tetrahedron: 2008; 64 6115
16. See also: Ozdemir I., Demir S., Cetinkaya B., Gourlaouen C., Maseras F., Bruneau C., Dixneuf P. H. J. Am. Chem. Soc.: 2008; 130 1156
17. See also: Ackermann L., Vicente R., Althammer A. Org. Lett.: 2008; 10 2299
18. See also: Oi S., Funayama R., Hattori T., Inoue Y. Tetrahedron: 2008; 64 6051
19. See also: Ackermann L., Born R., Vicente R. ChemSusChem: 2009; 2 546
20. See also: Ackermann L., Novák P. Org. Lett.: 2009; 11 4966
21. See also: Požgan F., Dixneuf P. H. Adv. Synth. Catal.: 2009; 351 1737
22. See also: Ackermann L., Novák P., Vicente R., Hofmann N. Angew. Chem. Int. Ed.: 2009; 48 6045
23. See also: Inoue S., Shiota H., Fukumoto Y., Chatani N. J. Am. Chem. Soc.: 2009; 131 6898
24. See also: Miura H., Wada K., Hosokawa S., Inoue M. Chem.-Eur. J.: 2010; 16 4186
25. See also: Arockiam P. B., Fischmeister C., Bruneau C., Dixneuf P. H. Angew. Chem. Int. Ed.: 2010; 49 6629
26. See also: Ackermann L., Novák P., Vicente R., Pirovano V., Potukuchi H. K. Synthesis: 2010; 2245
27. See also: Chan W.-W, Yeung S.-H, Zhou Z., Chan A. S. C, Yu W.-Y. Org. Lett.: 2010; 12 604
28. See also: Ackermann L., Vicente R., Potukuchi H. K., Pirovano V. Org. Lett.: 2010; 12 5032
29. See also: Flegeau E. F., Bruneau C., Dixneuf P. H., Jutand A. J. Am. Chem. Soc.: 2011; 133 10161
30. See also: Ackermann L., Lygin A. V. Org. Lett.: 2011; 13 3332
31. See also: Li B., Bheeter C. B., Darcel C., Dixneuf P. H. ACS Catal.: 2011; 1 1221
32. See also: Padala K., Jeganmohan M. Org. Lett.: 2012; 14 1134
33. See also: Chinnagolla R. K., Pimparker S., Jeganmohan M. Org. Lett.: 2012; 14 3032
34. Pd-catalyzed C-H activation: Brasche G., Garcia-Fortanet J., Buchwald S. L. Org. Lett.: 2008; 10 2207
35. See also: Campeau L.-C, Staurt D. R., Leclerc J.-P, Bertrand-Laperte M., Villemure E., Sun H.-Y, Lasserre S., Guimond N., Lecavallier M., Fagnou K. J. Am. Chem. Soc.: 2009; 131 3291
36. See also: Lapointe D., Fagnou K. Org. Lett.: 2009; 11 4160
37. See also: Mukai T., Hirano K., Satoh T., Miura M. Org. Lett.: 2010; 12 1360
38. See also: Wasa M., Worrel B. T., Yu J.-Q. Angew. Chem. Int. Ed.: 2010; 49 1275
39. See also: Nishikata T., Abela A. R., Lipshutz B. H. Angew. Chem. Int. Ed.: 2010; 49 781
40. Seo A., Tohnishi M., Nakao H., Furuya T., Kodama H., Tsubata K., Fujioka S., Kodama H., Nishimatsu T., Hirooka T. In Pesticide Chemistry. Ohkawa H., Miyagawa H., Lee P. W. Wiley-VCH Weinheim: 2007; 127 135
41. Ouellet S. G., Roy A., Molinaro C., Angelaud R., Marcoux J.-F, OShea P. D., Davies I. W. J. Org. Chem.: 2011; 76 1436
42. Seki M. ACS Catal.: 2011; 1 607
43. Seki M., Nagahama M. J. Org. Chem.: 2011; 76 10198
44. Mihina J. S., Herbst R. M. J. Org. Chem.: 1950; 15 1082
45. Russel R. G. Ann. N.Y. Acad. Sci.: 2006; 1068 367
46. Daemmrich A. A., Bowden M. E. Chem. Eng. News: 2005; 83 No. 25 70
47. Binkley N., Ringe J. P., Reed J. J., Ljunggren O., Holick M. F., Minne H. W., Liu M., Lamotta A., West J. A., Santora A. C. Bone: 2009; 44 639
48. Lan G., Peng L., Xie X., Peng F., Wang Y., Yu S. Transplant. Proc.: 2008; 40 3496
49. Mawatari T., Miura H., Hamai S., Shuto T., Nakashima Y., Okazaki K., Kinukawa N., Sakai S., Hoffmann P. F., Iwamoto Y., Keaveny T. M. Arthritis Rheum.: 2008; 58 3340