HRID230543

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID433294

Lithium chloride

ClLi

HCID2773552

4-Nitrophenylboronic acid

C6H6BNO4

HCID4715017

Ethyl 3-bromo-1H-indole-2-carboxylate

C11H10BrNO2

PRODUCTS

生成物

结构：CCOC(=O)c1[nH]c2ccccc2c1-c1ccc([N+](=O)[O-])cc1

HCID12404967

未命名化合物

收率 88.1%

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID702

Ethanol

C2H6O

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

46 ml of a 1M sodium carbonate solution, 2.23 g of lithium chloride and then 1.1 g of tetrakis(triphenylphosphine)palladium are added successively, under argon and with stirring, to a solution of 5 g of ethyl 3-bromo-1H-indole-2-carboxylate and 7.8 g of 4-nitrophenylboronic acid in 110 ml of ethanol and 110 ml of toluene. The solution is refluxed for 2 hours 30 minutes and then concentrated under reduced pressure. The precipitate is filtered off and then recrystallized from ethanol, to give 5.1 g of ethyl 3-(4-nitrophenyl)-1H-indole-2-carboxylate, the characteristics of which are as follows:

WORKUP

后处理

temperatureThe solution is refluxed for 2 hours 30 minutes
concentrationconcentrated under reduced pressure
filtrationThe precipitate is filtered off
customrecrystallized from ethanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-29229428bcbd4e8bb2c92168487decd3
来源数据集: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07566736B2
来源说明: uspto-grants-2009_07

反应 SMILES

C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+].Br[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[N+:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)([O-:26])=[O:25]>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:29][CH:28]=1)([O-:26])=[O:25]