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【结 构 式】

【分子编号】50432

【品名】1-ethyl-2-(hydroxymethyl)-1H-indole-6-carbonitrile

【CA登记号】

【 分 子 式 】C12H12N2O

【 分 子 量 】200.24016

【元素组成】C 71.98% H 6.04% N 13.99% O 7.99%

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:(VI)

Electrophilic nitration of p-tolunitrile (I) afforded the 3-nitro derivative (II), which was condensed with diethyl oxalate in the presence of sodium ethoxide to produce the sodium enolate of the alpha-keto ester (III). Compound (III) was then subjected to Reissert indole synthesis by means of Zn and HOAc to furnish ethyl 6-cyanoindole-2-carboxylate (IV). N-alkylation of indole (IV) with iodoethane and NaH in DMF gave (V), whose carboxylate group was reduced to alcohol (VI) employing in situ-generated calcium borohydride (obtained from NaBH4 and CaI2 in THF in the presence of NaHCO3). Treatment of alcohol (VI) with PBr3 in methylene chloride yielded the corresponding bromide (VII), which was then converted into the phosphonium salt (VIII) by means of triphenylphosphine in refluxing toluene.

1 Koo, B.A.; Min, J.K.; Hong, W.S.; Ryu, E.J.; Nam, W.H.; Kim, J.M. (C & C Research Laboratories); Aromatic amidine derivs. useful as selective thrombin inhibitors. EP 0918768; JP 2000504030; US 6201006; WO 9745424 .
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) 15458 4-methylbenzonitrile; p-tolunitrile 104-85-8 C8H7N 详情 详情
(II) 50428 4-methyl-3-nitrobenzonitrile C8H6N2O2 详情 详情
(III) 50429 sodium (Z)-1-(4-cyano-2-nitrophenyl)-3-ethoxy-3-oxo-1-propen-2-olate C12H9N2NaO5 详情 详情
(IV) 50430 ethyl 6-cyano-1H-indole-2-carboxylate C12H10N2O2 详情 详情
(V) 50431 ethyl 6-cyano-1-ethyl-1H-indole-2-carboxylate C14H14N2O2 详情 详情
(VI) 50432 1-ethyl-2-(hydroxymethyl)-1H-indole-6-carbonitrile C12H12N2O 详情 详情
(VII) 50433 2-(bromomethyl)-1-ethyl-1H-indole-6-carbonitrile C12H11BrN2 详情 详情
(VIII) 50434 [(6-cyano-1-ethyl-1H-indol-2-yl)methyl](triphenyl)phosphonium bromide C30H26BrN2P 详情 详情
Extended Information