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【结 构 式】 
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【分子编号】25956 【品名】2-bromo-1-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-ol 【CA登记号】 |
【 分 子 式 】C12H13BrOS 【 分 子 量 】285.20462 【元素组成】C 50.54% H 4.59% Br 28.02% O 5.61% S 11.24% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(VIII)The condensation of 2-bromo-2-cyclopentenone (II) with the aryl lithium compound (V) gives the tertiary alcohol (VIII), which is submitted to an oxidation with PDC with simultaneous allylic transposition to provide 2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one (IX). The oxidation of (IX) with H2O2 (Na2WO4) or MCPBA yields the corresponding sulfone (X), which is finally condensed with boronic acid (III) by means of a Pd catalyst as before. The synthetic approaches can also be performed with the arylmagnesium analogue of lithium derivative (V).
| 【1】 Black, C. (Merck Frosst Canada Inc.); 2-(3,5-Difluorophenyl)-3-(4-(methyl-sulfonyl)phenyl)-2-cyclopenten-1-one useful as an inhibitor of cyclooxygenase-2. EP 0863134; JP 1998251220 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 25951 | 2-bromo-2-cyclopenten-1-one | C5H5BrO | 详情 | 详情 | |
| (III) | 25952 | 3,5-difluorophenylboronic acid | 156545-07-2 | C6H5BF2O2 | 详情 | 详情 |
| (V) | 18808 | [4-(methylsulfanyl)phenyl]lithium | C7H7LiS | 详情 | 详情 | |
| (VIII) | 25956 | 2-bromo-1-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-ol | C12H13BrOS | 详情 | 详情 | |
| (IX) | 25957 | 2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one | C12H11BrOS | 详情 | 详情 | |
| (X) | 25958 | 2-bromo-3-[4-(methylsulfonyl)phenyl]-2-cyclopenten-1-one | C12H11BrO3S | 详情 | 详情 |
Extended Information