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【结 构 式】 
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【分子编号】12837 【品名】3-Chloro-7-methyl-1-benzothiophene 【CA登记号】 |
【 分 子 式 】C9H7ClS 【 分 子 量 】182.67328 【元素组成】C 59.18% H 3.86% Cl 19.41% S 17.55% |
合成路线1
该中间体在本合成路线中的序号：(III)A new synthesis of SDZ-87469 has been published: The chlorination of 7-methylbenzo[b]thiophene (I) gives 2,3-dichloro-7-methylbenzo[b]thiophene (II), which is selectively dechlorinated with butyllithium and hydrolysis, yielding 3-chloro-7-methylbenzo[b]thiophene (III). The bromination of (III) with N-bromosuccinimide (NBS) in DMF affords 7-(bromomethyl)-3-chlorobenzo[b]thiophene (IV), which is finally condensed with N,6,6-trimethylhep-2-en-4-yn-1-amine (V) (E + Z mixture) by means of K2CO3 in DMF. The pure E-isomer is obtained by crystallization of the E + Z mixture of the hydrochlorides in ethanol. Amine (V) is obtained by reaction of the corresponding bromo derivative (IV) with methylamine.
| 【1】 Petranyi, G.; Stutz, A.; J Med Chem 1984, 27, 12, 1539-43. |
| 【2】 Stutz, A.; Nussbaumer, P.; Rev Iberoam Micol 1988, 5, 1, 89. |
| 【3】 Loozen, H.; Godefroi, E.; J Org Chem 1973, 38, 5, 1056-7. |
| 【4】 Stutz, A. (Novartis Deutschland GmbH); New allylamines and their use.. DE 3302814 . |
| 【5】 Nussbaumer, P.; Petranyi, G.; Stutz, A.; Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics. J Med Chem 1991, 34, 1, 65-73. |
| 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) | 12835 | 7-Methyl-1-benzothiophene | C9H8S | 详情 | 详情 | |
| (II) | 12836 | 2,3-Dichloro-7-methyl-1-benzothiophene | C9H6Cl2S | 详情 | 详情 | |
| (III) | 12837 | 3-Chloro-7-methyl-1-benzothiophene | C9H7ClS | 详情 | 详情 | |
| (IV) | 12838 | 7-(Bromomethyl)-3-chloro-1-benzothiophene | C9H6BrClS | 详情 | 详情 | |
| (V) | 12839 | N-[(E)-6,6-Dimethyl-2-hepten-4-ynyl]-N-methylamine; (E)-N,6,6-Trimethyl-2-hepten-4-yn-1-amine | C10H17N | 详情 | 详情 | |
| (VI) | 10109 | (E)-1-Bromo-6,6-dimethyl-2-hepten-4-yne | 78629-21-7 | C9H13Br | 详情 | 详情 |