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【结 构 式】 
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【药物名称】 【化学名称】3-[3-Ethoxy-3-oxo-1(E)-propenyl]-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester 【CA登记号】 【 分 子 式 】C15H16N2O4 【 分 子 量 】288.30577 |
【开发单位】CNRS (Originator), Sanofi-synthélabo (Originator) 【药理作用】Pharmacological Tools, GABA(A) Receptor Modulators |
合成路线1
Ethyl 6-azaindole-3-carboxylate (I) was formylated using dichloromethyl methyl ether and AlCl3 to provide aldehyde (II). Nitrogen protection in (II) with benzenesulfonyl chloride and NaH gave sulfonyl derivative (III). Subsequent Wittig condensation of (III) with (ethoxycarbonylmethylene)triphenyl phosphorane produced the unsaturated ester (IV). Finally, removal of the benzenesulfonyl protecting group of (IV) was effected by treatment with ethanolic NaOEt.
| 【1】 Le Hyaric, M.; Doisy, X.; Dekhane, M.; et al.; Synthesis and benzodiazepine receptor (omega receptor) affinities of 3-substituted derivatives of pyrrolo[2,3-c]pyridine-5-carboxylate, a novel class of omega1 selective ligands. Bioorg Med Chem 1999, 7, 5, 921. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 14182 | ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane | 1099-45-2 | C22H21O2P | 详情 | 详情 | |
| 14713 | benzenesulfonyl chloride | 98-09-9 | C6H5ClO2S | 详情 | 详情 | |
| 40668 | dichloro(methoxy)methane; dichloromethyl methyl ether | 4885-02-3 | C2H4Cl2O | 详情 | 详情 | |
| (I) | 26182 | ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylate | C10H10N2O2 | 详情 | 详情 | |
| (II) | 26183 | ethyl 3-formyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylate | C11H10N2O3 | 详情 | 详情 | |
| (III) | 26184 | ethyl 3-formyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate | C17H14N2O5S | 详情 | 详情 | |
| (IV) | 26185 | ethyl 3-[(E)-3-ethoxy-3-oxo-1-propenyl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate | C21H20N2O6S | 详情 | 详情 |
Extended Information