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【结 构 式】

【分子编号】29422

【品名】5-butyl-2-thienylboronic acid

【CA登记号】

【 分 子 式 】C8H13BO2S

【 分 子 量 】184.06702

【元素组成】C 52.2% H 7.12% B 5.87% O 17.38% S 17.42%

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:(VII)

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