HRID1531539

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

HCID2734349

3,5-Dimethylphenylboronic acid

C8H11BO2

结构：O=C1c2ccccc2C(=O)N1CCc1c(Br)[nH]c2ccc(OCc3ccccc3)cc12

HCID21254081

未命名化合物

PRODUCTS

生成物

结构：Cc1cc(C)cc(-c2[nH]c3ccc(OCc4ccccc4)cc3c2CCN2C(=O)c3ccccc3C2=O)c1

HCID21254056

未命名化合物

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

To a solution of 2-[2-(5-benzyloxy-2-bromo-1H-indol-3-yl)ethyl]isoindole-1,3-dione (500 mg in a mixture of 6 mL ethanol and 16 mL toluene) was added 3,5-dimethylphenyl boronic acid (205 mg) followed by 2.7 mL of 1M sodium carbonate. To the stirred solution was added lithium chloride (156 mg) followed by tetrakis(triphenylphosphine)palladium (78 mg) and the mixture heated to reflux on an oil bath. After 2 hours the mixture was cooled to room temperature and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane:methylene chloride:ethyl acetate, 15:8:1 then 12:8:1) gave the title compound (479 mg).

WORKUP

后处理

temperaturethe mixture heated
temperatureto reflux on an oil bath
concentrationconcentrated in vacuo
customPurification by flash chromatography on silica gel (hexane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-83f7171bde634a6b9e92a4cc5554f138
来源数据集: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06197975B1
来源说明: uspto-grants-2001_03

反应 SMILES

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](Br)=[C:12]2[CH2:19][CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[C:37]([CH3:39])[CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>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>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:35]1[CH:36]=[C:37]([CH3:39])[CH:38]=[C:33]([CH3:32])[CH:34]=1)=[C:12]2[CH2:19][CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1