1-[tert-butyl(dimethyl)silyl]-1H-indol-5-yl methyl ether; 1-[tert-butyl(dimethyl)silyl]-5-methoxy-1H-indole -Drug Synthesis Database

【结构式】

【分子编号】31541

【品名】1-[tert-butyl(dimethyl)silyl]-1H-indol-5-yl methyl ether; 1-[tert-butyl(dimethyl)silyl]-5-methoxy-1H-indole

【CA登记号】

【分子式】C₁₅H₂₃NOSi

【分子量】261.43926

【元素组成】C 68.91% H 8.87% N 5.36% O 6.12% Si 10.74%

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：(V)

Alternatively, 5-methoxyindole (III) was N-silylated employing tert-butyldimethylsilyl chloride and n-BuLi, and the resulting silyl derivative (V) was brominated with N-bromosuccinimide at -78 C to afford the 3-bromoindole (VI). After lithium-bromine exchange in (VI) with n-BuLi at -78 C, the 3-lithio compound was condensed with N-methyl-D-proline methyl ester (VII) to give the indolyl ketone (VIII). The ketone function of (VIII) was finally reduced employing LiAlH4 in boiling THF.

参考文献中间体

合成目标

【1】 Qandil, A.M.; Marona-Lewicka, D.; Gerasimov, M.; Kurrasch-Orbaugh, D.M.; Nichols, D.E.; Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain. J Med Chem 1999, 42, 20, 4257.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	25902	1H-Indol-5-yl methyl ether; 5-Methoxy-1H-indole; 5-Methoxyindole	1006-94-6	C₉H₉NO	详情	详情
(V)	31541	1-[tert-butyl(dimethyl)silyl]-1H-indol-5-yl methyl ether; 1-[tert-butyl(dimethyl)silyl]-5-methoxy-1H-indole		C₁₅H₂₃NOSi	详情	详情
(VI)	31542	3-bromo-1-[tert-butyl(dimethyl)silyl]-5-methoxy-1H-indole; 3-bromo-1-[tert-butyl(dimethyl)silyl]-1H-indol-5-yl methyl ether		C₁₅H₂₂BrNOSi	详情	详情
(VII)	31538	methyl (2R)-1-methyl-2-pyrrolidinecarboxylate		C₇H₁₃NO₂	详情	详情
(VIII)	31543	(5-methoxy-1H-indol-3-yl)[(2R)-1-methylpyrrolidinyl]methanone		C₁₅H₁₈N₂O₂	详情	详情

Extended Information