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【结 构 式】 
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【分子编号】30005 【品名】Triisopropoxy(3-pyridyl)boranuide lithium salt 【CA登记号】 |
【 分 子 式 】C14H25BLiNO3 【 分 子 量 】273.10944 【元素组成】C 61.57% H 9.23% B 3.96% Li 2.54% N 5.13% O 17.57% |
合成路线1
该中间体在本合成路线中的序号：(VII)The bromination of 3-ethoxy-2-cyclopenten-1-one (I) with Br2 and triethylamine in chloroform gives the 2-bromo derivative (II), which is condensed with 4-bromothioanisole (III) by means of BuLi in THF yielding 2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one (IV). The oxidation of (IV) with Na2WO4 and H2O2 affords the corresponding sulfone (V), which is finally condensed with lithium diisopropyl 3-pyridylboronate (VII) or the corresponding dimethyl ester (VIII) by means of tris(dibenzylideneacetone)dipalladium (III) (Pd2(dba)3) and triphenylphosphine in toluene/propanol/water. The lithium boronates (VII) and (VIII) have been obtained by reaction of 3-bromopyridine (VI) with triisopropyl borate or trimethyl borate and BuLi in ethyl ether.
| 【1】 Chan, C.-C.; Brideau, C.; Black, W.C.; et al.; 2,3-Diarylcyclopentenones as orally active, highly selective cyclooxygenase-2 inhibitors. J Med Chem 1999, 42, 7, 1274. |
| 【2】 Black, C.; Hughes, G.; Wang, Z. (Merck Frosst Canada Inc.); Pyridinyl-2-cyclopenten-1-ones as selective cyclooxygenase-2 inhibitors. EP 0900201; JP 2000509032; US 5922742; WO 9740012 . |
| 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) | 25959 | 3-ethoxy-2-cyclopenten-1-one | C7H10O2 | 详情 | 详情 | |
| (II) | 25960 | 2-bromo-3-ethoxy-2-cyclopenten-1-one | C7H9BrO2 | 详情 | 详情 | |
| (III) | 19266 | 4-bromophenyl methyl sulfide; 1-bromo-4-(methylsulfanyl)benzene | 104-95-0 | C7H7BrS | 详情 | 详情 |
| (IV) | 25957 | 2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one | C12H11BrOS | 详情 | 详情 | |
| (V) | 25958 | 2-bromo-3-[4-(methylsulfonyl)phenyl]-2-cyclopenten-1-one | C12H11BrO3S | 详情 | 详情 | |
| (VI) | 13265 | 3-Bromopyridine | 626-55-1 | C5H4BrN | 详情 | 详情 |
| (VII) | 30005 | Triisopropoxy(3-pyridyl)boranuide lithium salt | C14H25BLiNO3 | 详情 | 详情 | |
| (VIII) | 30006 | Trimethoxy(3-pyridyl)boranuide lithium salt | C8H13BLiNO3 | 详情 | 详情 |