HRID449535

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID10796

Cesium carbonate

CCs2O3

HCID46738957

5-(3-Boronophenyl)pentanoic acid

C11H15BO4

结构：CC1(C)C(/C=C/C(Br)=C/C=C2/N(CCCS(=O)(=O)[O-])c3ccc4c(S(=O)(=O)[O-])cc(S(=O)(=O)[O-])cc4c3C2(C)C)=[N+](CCCS(=O)(=O)[O-])c2ccc3c(S(=O)(=O)[O-])cc(S(=O)(=O)[O-])cc3c21.[Na+].[Na+].[Na+].[Na+].[Na+]

HCID86649203

未命名化合物

PRODUCTS

生成物

结构：CC1(C)C(/C=C/C(=C/C=C2/N(CCCS(=O)(=O)[O-])c3ccc4c(S(=O)(=O)[O-])cc(S(=O)(=O)[O-])cc4c3C2(C)C)c2cccc(CCCCC(=O)O)c2)=[N+](CCCS(=O)(=O)[O-])c2ccc3c(S(=O)(=O)[O-])cc(S(=O)(=O)[O-])cc3c21.[Na+].[Na+].[Na+].[Na+].[Na+]

HCID86649207

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

PROCEDURE

实验过程

Compound 6 (80 mg), 3-(4-carboxybutyl)phenylboronic acid (40 mg), and cesium carbonate (20 mg) are stirred into 1:1 water:ethanol (10 ml) under nitrogen at room temperature. Tetrakis(triphenylphosphine)palladium(0) (10 mg) is added to the reaction mixture. The mixture was refluxed for 4 hours, and the solvent and volatile compounds are evaporated under vacuum. The crude product is purified by flash chromatography on reverse-phase C18-functionalized silica by eluting with a 1:4 acetonitrile:water mixture. The purified product 8 has UV/vis absorption max of λMeOH=680 nm, ε=229,000; λPBS676 nm, ε=239,000.

WORKUP

后处理

customat room temperature
temperatureThe mixture was refluxed for 4 hours
customthe solvent and volatile compounds are evaporated under vacuum
customThe crude product is purified by flash chromatography on reverse-phase C18-functionalized silica
washby eluting with a 1:4 acetonitrile
customUV/vis absorption max of λMeOH=680 nm, ε=229,000

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e580f60a63104e9b81a2a32dac8f6b67
来源数据集: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08481752B2
来源说明: uspto-grants-2013_07

反应 SMILES

Br/[C:2](=[CH:35]\[CH:36]=[C:37]1\[N:38]([CH2:60][CH2:61][CH2:62][S:63]([O-:66])(=[O:65])=[O:64])[C:39]2[CH:40]=[CH:41][C:42]3[C:51]([S:52]([O-:55])(=[O:54])=[O:53])=[CH:50][C:49]([S:56]([O-:59])(=[O:58])=[O:57])=[CH:48][C:43]=3[C:44]=2[C:45]\1([CH3:47])[CH3:46])/[CH:3]=[CH:4]/[C:5]1[C:13]([CH3:15])([CH3:14])[C:12]2[C:11]3[CH:16]=[C:17]([S:24]([O-:27])(=[O:26])=[O:25])[CH:18]=[C:19]([S:20]([O-:23])(=[O:22])=[O:21])[C:10]=3[CH:9]=[CH:8][C:7]=2[N+:6]=1[CH2:28][CH2:29][CH2:30][S:31]([O-:34])(=[O:33])=[O:32].[Na+:67].[Na+].[Na+].[Na+].[Na+].[C:72]([CH2:75][CH2:76][CH2:77][CH2:78][C:79]1[CH:80]=[C:81](B(O)O)[CH:82]=[CH:83][CH:84]=1)([OH:74])=[O:73].C(=O)([O-])[O-].[Cs+].[Cs+].O>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.C(O)C>[C:72]([CH2:75][CH2:76][CH2:77][CH2:78][C:79]1[CH:80]=[C:81](/[C:2](=[CH:35]\[CH:36]=[C:37]2\[N:38]([CH2:60][CH2:61][CH2:62][S:63]([O-:66])(=[O:65])=[O:64])[C:39]3[CH:40]=[CH:41][C:42]4[C:51]([S:52]([O-:55])(=[O:54])=[O:53])=[CH:50][C:49]([S:56]([O-:59])(=[O:57])=[O:58])=[CH:48][C:43]=4[C:44]=3[C:45]\2([CH3:47])[CH3:46])/[CH:3]=[CH:4]/[C:5]2[C:13]([CH3:14])([CH3:15])[C:12]3[C:11]4[CH:16]=[C:17]([S:24]([O-:27])(=[O:25])=[O:26])[CH:18]=[C:19]([S:20]([O-:23])(=[O:21])=[O:22])[C:10]=4[CH:9]=[CH:8][C:7]=3[N+:6]=2[CH2:28][CH2:29][CH2:30][S:31]([O-:34])(=[O:32])=[O:33])[CH:82]=[CH:83][CH:84]=1)([OH:74])=[O:73].[Na+:67].[Na+:67].[Na+:67].[Na+:67].[Na+:67]