6-bromo-1-(triisopropylsilyl)-1H-indole -Drug Synthesis Database

【结构式】

【分子编号】47471

【品名】6-bromo-1-(triisopropylsilyl)-1H-indole

【CA登记号】

【分子式】C₁₇H₂₆BrNSi

【分子量】352.38968

【元素组成】C 57.94% H 7.44% Br 22.67% N 3.97% Si 7.97%

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)

The reaction of 6-bromo-1H-indole (I) with Tips-Cl and NaH in DMF gives the N-silylated indole (II), which is condensed with 1,4-diazabicyclo[4,3,0]nonane (III) by means of tBu-ONa, Pd(OAc)2 and tBu3P in hot xylene to yield the corresponding adduct (IV). The desilylation of (IV) by means of TBAF in THF affords the deprotected indole (V), which is finally sulfonated with 1-naphthylsulfonyl chloride and NaHMDS in THF.

参考文献中间体

合成目标

【1】 Isaac, M.; et al.; 6-Bicyclopiperazinyl-1-araylsulfonylindoles and 6-bicyclopiperidinyl-1-arylsulfonylindoles derivatives as novel, potent, and selective 5-HT6 receptor antagonists. Bioorg Med Chem Lett 2000, 10, 15, 1719.
【2】 Isaac, M.; Slassi, A.; Xin, T. (NPS Allelix Corp.); Cpds. having 5-HT6 receptor antagonist activity. WO 0132660 .

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)	30014	6-Bromoindole; 6-Bromo-1H-indole	52415-29-9	C₈H₆BrN	详情	详情
(II)	47471	6-bromo-1-(triisopropylsilyl)-1H-indole		C₁₇H₂₆BrNSi	详情	详情
(III)	40336	octahydropyrrolo[1,2-a]pyrazine		C₇H₁₄N₂	详情	详情
(IV)	47472	2-[1-(triisopropylsilyl)-1H-indol-6-yl]octahydropyrrolo[1,2-a]pyrazine		C₂₄H₃₉N₃Si	详情	详情
(V)	47473	2-(1H-indol-6-yl)octahydropyrrolo[1,2-a]pyrazine		C₁₅H₁₉N₃	详情	详情
(VI)	18650	1-naphthalenesulfonyl chloride	85-46-1	C₁₀H₇ClO₂S	详情	详情

Extended Information