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【结 构 式】

【分子编号】10873

【品名】8-Bromo-9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

【CA登记号】

【 分 子 式 】C14H11BrFNO3

【 分 子 量 】340.1486832

【元素组成】C 49.44% H 3.26% Br 23.49% F 5.59% N 4.12% O 14.11%

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:(V)

The bromination of 5-fluoro-2-methylquinoline (I) with Br2 and Ag2SO4 in H2SO4 or with Br2 and AlCl3 gives 5-bromo-6-fluoro-2-methylquinoline (II), which is reduced with H2 over PtO2 in acetic acid, yielding 5-bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (III). The cyclization of (III) with diethyl ethoxymethylenemalonate (IV) and polyphosphoric acid (PPA) at 150 C affords 8-bromo-9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (V), which is finally condensed with 4-hydroxypiperidine (VI) by heating at 160 C in HMPT.

1 Kano, M.; Nakagawa, K.; Ishikawa, H.; Uno, T. (Otsuka Pharmaceutical Co., Ltd.); Antibacterial agents. JP 1983090511 .
2 Bernauer, K.; Borgulya, J.; Bruderer, H.; Da Prada, M.; Zurcher, G. (F. Hoffmann-La Roche AG); 3,5-Disubstituted pyrocatechol derivs. EP 0237929; US 5389653; US 5476875 .
3 Ishikawa, H.; Tabusa, F.; Miyamoto, H.; Kano, M.; Ueda, H.; Tamaoka, H.; Nakagawa, K.; Synthesis of substituted 6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acids. Chem Pharm Bull 1989, 37, 8, 2103-8.
4 Prous, J.; Castaner, J.; OPC-7251. Drugs Fut 1990, 15, 7, 685.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12076 4-Piperidinol; 4-Hydroxypiperidine 5382-16-1 C5H11NO 详情 详情
(I) 10869 6-Fluoro-2-methylquinoline 1128-61-6 C10H8FN 详情 详情
(II) 10870 5-Bromo-6-fluoro-2-methylquinoline C10H7BrFN 详情 详情
(III) 10871 5-Bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline C10H11BrFN 详情 详情
(IV) 10872 diethyl 2-[(E)-ethoxymethylidene]succinate C11H18O5 详情 详情
(V) 10873 8-Bromo-9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid C14H11BrFNO3 详情 详情
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