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【结 构 式】 
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【分子编号】46621 【品名】5-(4'-methyl[1,1'-biphenyl]-2-yl)-2-trityl-2H-1,2,3,4-tetraazole 【CA登记号】 |
【 分 子 式 】C33H26N4 【 分 子 量 】478.5964 【元素组成】C 82.82% H 5.48% N 11.71% |
合成路线1
该中间体在本合成路线中的序号：(VI)The cyclization of benzonitrile (I) with sodium azide by means of ZnCl2 in hot DMF gives 5-phenyltetrazole (II), which is condensed with trityl chloride (III) by means of TEA in THF to yield 5-phenyl-2-(triphenylmethyl)tetrazole (IV). The condensation of (IV) with 4-iodotoluene (V) by means of n-BuLi, ZnCl2, (PPh3)2NiCl2 and CH3MgCl in THF affords 5-(4'-methylbiphenyl-2-yl)-2-triphenylmethyltetrazole ?VI), which is finally brominated with N-bromosuccinimide (NBS) and AIBN in refluxing acetic acid to provide the target intermediate 5-[4'-(bromomethyl)biphenyl-2-yl]-2-(triphenylmethyl)tetrazole (VII).
| 【1】 Fisher, M.H.; Wyvratt, M.J.; Schoen, W.R.; DeVita, R.J. (Merck & Co., Inc.); Benzo-fused lactams promote release of growth hormone. EP 0513974; JP 1994172316; US 5206235; WO 9216524 . |
| 【2】 Anderson, R.K.; King, A.O.; Shuman, R.F. (Merck & Co., Inc.); Ortho-lithiation process for the synthesis of 2-substd. 1-(tetrazol-5-yl)benzenes. US 5039814 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 25904 | benzonitrile | 100-47-0 | C7H5N | 详情 | 详情 |
| (II) | 36353 | 5-phenyl-2H-1,2,3,4-tetraazole | 18039-42-4 | C7H6N4 | 详情 | 详情 |
| (III) | 28630 | Triphenylchloromethane; 1-[Chloro(diphenyl)methyl]benzene; Trityl chloride | 76-83-5 | C19H15Cl | 详情 | 详情 |
| (IV) | 36354 | 5-phenyl-2-trityl-2H-1,2,3,4-tetraazole | C26H20N4 | 详情 | 详情 | |
| (V) | 46620 | 1-iodo-4-methylbenzene | C7H7I | 详情 | 详情 | |
| (VI) | 46621 | 5-(4'-methyl[1,1'-biphenyl]-2-yl)-2-trityl-2H-1,2,3,4-tetraazole | C33H26N4 | 详情 | 详情 | |
| (VII) | 15538 | 5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-trityl-2H-1,2,3,4-tetraazole | 124750-51-2 | C33H25BrN4 | 详情 | 详情 |