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Convergent Synthesis of Angiotensin II Receptor Blockers through C–H Arylation of 1-Benzyl-5-phenyl-1H-tetrazole with Functionalized Aryl Bromides
| Content Provider | Scilit |
|---|---|
| Author | Seki, Masahiko Takahashi, Yusuke |
| Copyright Year | 2021 |
| Description | Highly convergent synthesis of angiotensin II receptor blockers has been accomplished by means of late-stage C–H arylation using functionalized aryl bromides. C–H arylation of 1-benzyl-5-phenyl-1H-tetrazole with aryl bromides carrying methyl 2-ethoxybenzimidazole-7-carboxylate unexpectedly provided coupling products where ethyl group was migrated from oxygen to nitrogen atom. The O-to-N ethyl migration was completely suppressed by the use of N-pivaloyl-l-valine rather than the combined use of triphenylphosphine and sodium mesitylenesulfonate to result in the preferential formation of a key intermediate of candesartan cilexetil. In contrast, when an aryl bromide having ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate was employed, the C–H arylation proceeded smoothly to provide a late-stage intermediate, which rapidly led to olmesartan medoxomil in 3 steps. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1472-0925.pdf |
| Ending Page | 2692 |
| Page Count | 4 |
| Starting Page | 2689 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/a-1472-0925 |
| Journal | Synthesis |
| Issue Number | 15 |
| Volume Number | 53 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2021-03-31 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
