2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride -Drug Synthesis Database

【结构式】

【分子编号】40925

【品名】2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride

【CA登记号】

【分子式】C₁₀H₅BrClNO₂

【分子量】286.51194

【元素组成】C 41.92% H 1.76% Br 27.89% Cl 12.37% N 4.89% O 11.17%

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：(II)

Condensation of 5-bromoindole (I) with oxalyl chloride produced (5-bromo-3-indolyl)glyoxyl chloride (II), which was subsequently treated with dimethylamine to give amide (III). Conversion of (III) to the tributylstannyl derivative (IV) was achieved by reaction with hexabutylditin in the presence of tetrakis(triphenylphosphine) palladium in refluxing dimethoxyethane. Palladium-catalyzed coupling of stannyl indole (IV) with 5-bromo-2-thiophenecarboxaldehyde (V) furnished the thienyl indole (VI). Finally, reduction of (VI) with LiAlH4 in boiling THF produced a mixture of the desired 5-methylthiophene derivative along with the 5-(hydroxymethyl) analogue (VII), that were separated by column chromatography.

参考文献中间体

合成目标

【1】 Kamboj, R.; Slassi, A.; Mazzocco, L.; Meng, C.Q.; Lee, D.K.H.; Dyne, K.; McCallum, K.L.; Rakhit, S.; 5-Thienyltryptamine derivatives as serotonin 5-HT1B/1D receptor agonists: Potential treatments for migraine. Bioorg Med Chem Lett 2000, 10, 9, 903.
【2】 Meng, Q.; Slassi, A.; Rakhit, S. (NPS Allelix Corp.); Thiophene- and furan-tryptamine derivs.. WO 9743281 .

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)	13309	5-Bromo-1H-indole; 5-Bromoindole	10075-50-0	C₈H₆BrN	详情	详情
(II)	40925	2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride		C₁₀H₅BrClNO₂	详情	详情
(III)	40926	2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide		C₁₂H₁₁BrN₂O₂	详情	详情
(IV)	40927	N,N-dimethyl-2-oxo-2-[5-(tributylstannyl)-1H-indol-3-yl]acetamide		C₂₄H₃₈N₂O₂Sn	详情	详情
(V)	40928	5-bromo-2-thiophenecarbaldehyde	4701-17-1	C₅H₃BrOS	详情	详情
(VI)	40929	2-[5-(5-formyl-2-thienyl)-1H-indol-3-yl]-N,N-dimethyl-2-oxoacetamide		C₁₇H₁₄N₂O₃S	详情	详情
(VII)	40930	(5-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-2-thienyl)methanol		C₁₇H₂₀N₂OS	详情	详情

Extended Information