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【结 构 式】 
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【分子编号】29419 【品名】2-(4-bromo-2-fluorophenyl)-1-(4-pyridinyl)-1-ethanone 【CA登记号】 |
【 分 子 式 】C13H9BrFNO 【 分 子 量 】294.1230032 【元素组成】C 53.09% H 3.08% Br 27.17% F 6.46% N 4.76% O 5.44% |
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：(III)The alkylation of 4-(dimethoxymethyl)pyridine (I) with 4-bromo-2-fluorobenzyl bromide (II) in the presence of n-butyllithium, followed by ketal hydrolysis with formic acid provided the diaryl ethanone (III). Further alkylation of (III) with 4-chlorophenacyl bromide (IV) employing sodium hexamethyldisilazide yielded diketone (V), which was cyclized in the presence of ammonium acetate in boiling AcOH to produce pyrrole (VI). Finally, Suzuki coupling of (VI) with 5-butyl-2-thiopheneboronic acid (VII) by means of Pd(PPh3)4 furnished the title compound.
| 【1】 McMillan, M.; Cudaback, E.; Misra-Press, A.; et al.; Synthesis and biological studies of a novel inhibitor of NF-kappaB. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 213. |
| 【2】 De Laszlo, S.E.; Chang, L.L.; Kim, D.; Mantlo, N.B. (Merck & Co., Inc.); Substd. pyridyl pyrroles, compsns. containing such cpds. and methods of use. EP 0859771; JP 1999514651; WO 9716442 . |
| 【3】 de Laszlo, S.E.; Kim, D.; Chang, L.L.; Mantlo, N.B. (Merck & Co., Inc.); Substd. pyridyl pyrroles, compsns. containing such cpds. and methods of use. US 5776954 . |
| 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) | 29418 | 4-(dimethoxymethyl)pyridinemethoxy(4-pyridinyl)methyl methyl ether | C8H11NO2 | 详情 | 详情 | |
| (II) | 22904 | 2-fluoro-4-bromobenzyl bromide; 4-bromo-1-(bromomethyl)-2-fluorobenzene | 76283-09-5 | C7H5Br2F | 详情 | 详情 |
| (III) | 29419 | 2-(4-bromo-2-fluorophenyl)-1-(4-pyridinyl)-1-ethanone | C13H9BrFNO | 详情 | 详情 | |
| (IV) | 16720 | 2-bromo-1-(4-chlorophenyl)-1-ethanone; 2-Bromo-4'-chloroacetophenone | 536-38-9 | C8H6BrClO | 详情 | 详情 |
| (V) | 29420 | 2-(4-bromo-2-fluorophenyl)-4-(4-chlorophenyl)-1-(4-pyridinyl)-1,4-butanedione | C21H14BrClFNO2 | 详情 | 详情 | |
| (VI) | 29421 | 4-[3-(4-bromo-2-fluorophenyl)-5-(4-chlorophenyl)-1H-pyrrol-2-yl]pyridine | C21H13BrClFN2 | 详情 | 详情 | |
| (VII) | 29422 | 5-butyl-2-thienylboronic acid | C8H13BO2S | 详情 | 详情 |
Extended Information