2-bromo-6-(methyloxy)-5-(1,3-oxazol-5-yl)-1H-indole-3-carbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】64335

【品名】2-bromo-6-(methyloxy)-5-(1,3-oxazol-5-yl)-1H-indole-3-carbaldehyde

【CA登记号】

【分子式】C₁₃H₉BrN₂O₃

【分子量】321.13014

【元素组成】C 48.62% H 2.82% Br 24.88% N 8.72% O 14.95%

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)

Condensation of iodoaniline (I) with ethyl 2-(methylsulfanyl)acetate (II) in the presence of sulfuryl chloride gives rise to the oxindole derivative (III). Desulfuration of (III) by means of Raney-nickel then affords (IV). The Vilsmeier-Haack reaction of oxindole (IV) with POBr3 and DMF leads to the bromo aldehyde (V). This is finally subjected to Suzuki coupling with 3-benzothienylboronic acid (VI) to furnish the title compound.

参考文献中间体

合成目标

【1】 Watterson, S.H.; Dhar, T.G.M.; Ballentine, S.K.; Shen, Z.; Barrish, J.C.; Cheney, D.; Fleener, C.A.; Rouleau, K.A.; Townsend, C.; Hollenbaugh, D.L.; Iwanowicz, E.J.; Novel indole-based inhibitors of IMPDH: Introduction of hydrogen bond acceptors at indole C-3. Bioorg Med Chem Lett 2003, 13, 7, 1273.

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)	64043	2-iodo-5-(methyloxy)-4-(1,3-oxazol-5-yl)aniline; 2-iodo-5-(methyloxy)-4-(1,3-oxazol-5-yl)phenylamine		C₁₀H₉IN₂O₂	详情	详情
(II)	48543	Ethyl methylthioacetate; (Methylthio)acetic acid ethyl ester; ethyl 2-(methylsulfanyl)acetate	4455-13-4	C₅H₁₀O₂S	详情	详情
(III)	64333	6-(methyloxy)-3-(methylsulfanyl)-5-(1,3-oxazol-5-yl)-1,3-dihydro-2H-indol-2-one		C₁₃H₁₂N₂O₃S	详情	详情
(IV)	64334	6-(methyloxy)-5-(1,3-oxazol-5-yl)-1,3-dihydro-2H-indol-2-one		C₁₂H₁₀N₂O₃	详情	详情
(V)	64335	2-bromo-6-(methyloxy)-5-(1,3-oxazol-5-yl)-1H-indole-3-carbaldehyde		C₁₃H₉BrN₂O₃	详情	详情
(VI)	64336	1-benzothiophen-3-ylboronic acid		C₈H₇BO₂S	详情	详情

Extended Information