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【结 构 式】 
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【分子编号】62887 【品名】3,7-dibromo-1,2-benzisothiazole 【CA登记号】 |
【 分 子 式 】C7H3Br2NS 【 分 子 量 】292.98156 【元素组成】C 28.7% H 1.03% Br 54.55% N 4.78% S 10.94% |
合成路线1
该中间体在本合成路线中的序号：(III)The bromination of 3-chloro-1,2-benzoisothiazole (I) with Br2 in AcOH using FeCl3 as catalyst gives a mixture of 3,5-dibromo-1,2-benzoisothiazole (II) and 3,7-dibromo-1,2-benzoisothiazole (III) that are separated by flash chromatography. The desired isomer (III) is condensed with piperazine (IV) in refluxing diglyme to yield 7-bromo-3-(1-piperazinyl)-1,2-benzoisothiazole (V), which is condensed with 6-chloro-5-(2-chloroethyl)indolin-2-one (VI) by means of Na2CO3 in refluxing water to afford the brominated adduct (VII). Finally, this compound is debrominated with tritium gas over a Pd/BaSO4 catalyst in THF to provide the target radiolabeled compound.
| 【1】 Howard, H.R.; Shenk, K.D.; Smolarek, T.A.; Marx, M.H.; Windels, J.H.; Roth, R.W.; Synthesis of H-3- and C-14-labelled CP-88,059: A potent atypical antipsychotic agent. J Label Compd Radiopharm 1994, 34, 2, 117. |
| 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) | 16279 | 3-chloro-1,2-benzisothiazole | C7H4ClNS | 详情 | 详情 | |
| (II) | 62886 | 3,5-dibromo-1,2-benzisothiazole | C7H3Br2NS | 详情 | 详情 | |
| (III) | 62887 | 3,7-dibromo-1,2-benzisothiazole | C7H3Br2NS | 详情 | 详情 | |
| (IV) | 10355 | Diethylenediamine; Piperazine | 110-85-0 | C4H10N2 | 详情 | 详情 |
| (V) | 62888 | 7-bromo-3-(1-piperazinyl)-1,2-benzisothiazole | C11H12BrN3S | 详情 | 详情 | |
| (VI) | 16277 | 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one; 5-chloroethyl-6-chloro-1,3-dihydro-1H-indol-2-one- | C10H9Cl2NO | 详情 | 详情 | |
| (VII) | 62889 | 5-{2-[4-(7-bromo-1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one | C21H20BrClN4OS | 详情 | 详情 |