ethyl 3-[(E)-3-ethoxy-3-oxo-1-propenyl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】26185

【品名】ethyl 3-[(E)-3-ethoxy-3-oxo-1-propenyl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

【CA登记号】

【分子式】C₂₁H₂₀N₂O₆S

【分子量】428.46568

【元素组成】C 58.87% H 4.7% N 6.54% O 22.4% S 7.48%

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：(IV)

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.

参考文献中间体

合成目标

【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