HRID2361311

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：Cc1c(/C=C/[N+](=O)[O-])cccc1NC(=O)OCc1ccccc1

HCID67995173

未命名化合物

结构：CC(C)(C)[Si](C)(C)OC1CCN(c2ccc3cc[nH]c3c2)C1

HCID86681519

未命名化合物

PRODUCTS

生成物

结构：Cc1c(NC(=O)OCc2ccccc2)cccc1C(C[N+](=O)[O-])c1c[nH]c2cc(N3CCC(O[Si](C)(C)C(C)(C)C)C3)ccc12

HCID67994623

未命名化合物

收率 33.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度: 110 °C

PROCEDURE

实验过程

6-(3-(tert-Butyldimethylsilyloxy)pyrrolidin-1-yl)-1H-indole (1.867 g, 5.90 mmol) and (E)-benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate (1.5354 g, 4.92 mmol) were dissolved in THF (40 mL), concentrated in vacuo, and the mixture was heated at 110° C. for 1 hr. The reaction mixture was cooled to room temperature and purified by flash chromatography using an ISCO 220 g column eluting with 25-100% EtOAc/hexanes to give the desired product (1.0324 g, 1.642 mmol, 33.4% yield) as a tan solid.

WORKUP

后处理

concentrationconcentrated in vacuo
temperatureThe reaction mixture was cooled to room temperature
custompurified by flash chromatography
washeluting with 25-100% EtOAc/hexanes

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-457199af556f4c64bf3ca833ae89d96a
来源数据集: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08685969B2
来源说明: uspto-grants-2014_04

反应 SMILES

[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:23][C:24]1[C:29](/[CH:30]=[CH:31]/[N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=[CH:26][C:25]=1[NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1COCC1>[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([CH:30]([C:29]4[C:24]([CH3:23])=[C:25]([NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]5[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=5)[CH:26]=[CH:27][CH:28]=4)[CH2:31][N+:32]([O-:34])=[O:33])=[CH:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]