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【结 构 式】

【分子编号】19320

【品名】1-(2,3-dihydro-1H-indol-1-yl)-1-ethanone

【CA登记号】16078-30-1

【 分 子 式 】C10H11NO

【 分 子 量 】161.20348

【元素组成】C 74.51% H 6.88% N 8.69% O 9.92%

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:(I)

Friedel-Crafts acylation of 1-acetylindoline (I) with acetyl chloride and AlCl3 afforded ketone (II). Subsequent Baeyer-Villiger rearrangement using peracetic acid yielded acetate ester (III), which was hydrolyzed with NaOH to give phenol (IV). Bromination of (IV) with NBS in AcOH then provided bromo hydroxy indoline (V). Alkylation with 1-methyl-tetrahydropyridine-4-methanol (VI) under Mitsunobu conditions produced ether (VII). This was cyclized to the spirocyclic compound (VIII) using AIBN and tributyltin hydride in refluxing benzene. Then, amide hydrolysis in hydroalcoholic HCl gave (IX), which was finally condensed with acid chloride (X) to provide the desired amide.

1 Gaster, L.M.; et al.; The selective 5-HT1B receptor inverse agonist 1'-methyl-5-[[2'-methyl-4'-(5-methyl-1,2, 4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6, 7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (SB-224289) potently blocks terminal 5-HT autoreceptor function b. J Med Chem 1998, 41, 8, 1218.
2 Gaster, L.; et al.; SB-224289 - a highly selective 5-HT1B receptor inverse agonist. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.259.
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) 19320 1-(2,3-dihydro-1H-indol-1-yl)-1-ethanone 16078-30-1 C10H11NO 详情 详情
(II) 19321 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-1-ethanone C12H13NO2 详情 详情
(III) 19322 1-acetyl-2,3-dihydro-1H-indol-5-yl acetate C12H13NO3 详情 详情
(IV) 19323 1-(5-hydroxy-2,3-dihydro-1H-indol-1-yl)-1-ethanone C10H11NO2 详情 详情
(V) 19324 1-(6-bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)-1-ethanone C10H10BrNO2 详情 详情
(VI) 19325 (1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)methanol C7H13NO 详情 详情
(VII) 19326 1-[6-bromo-5-[(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)methoxy]-2,3-dihydro-1H-indol-1-yl]-1-ethanone C17H21BrN2O2 详情 详情
(VIII) 19327 5-Acetyl-1'-methyl-3,5,6,7-tetrahydro-2H-spiro[furo[2,3-f]indole-3,4'-piperidine] C17H22N2O2 详情 详情
(IX) 19328 1'-Methyl-3,5,6,7-tetrahydro-2H-spiro[furo[2,3-f]indole-3,4'-piperidine] C15H20N2O 详情 详情
(X) 19329 2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-carbonyl chloride C17H13ClN2O2 详情 详情
Extended Information