HRID1055877

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC

HCID619414

Tributyl(1-ethoxyvinyl)stannane

C16H34OSn

HCID89793625

未命名化合物

PRODUCTS

生成物

结构：COC(=O)N(c1ccccc1)c1ccc2cccc(C(C)=O)c2n1

HCID89793621

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HCID1140

Toluene

C7H8

CONDITIONS

反应条件

温度: 100 °C

PROCEDURE

实验过程

A mixture of Pd(PPh3)4 (60.8 mg, 0.053 mmol, Strem Chemicals, Newburyport, Mass.), tributyl(1-ethoxyvinyl)stannane (391 μl, 1.158 mmol, Sigma Aldrich), methyl (8-bromoquinolin-2-yl)(phenyl)carbamate (Example 46a; 376 mg, 1.053 mmol), and toluene (5.2 mL) were stirred under N2 at 100° C. for 20 h. Purification by column chromatography (silica gel: 0 to 10% EtOAc/hexanes followed by 70% EtOAc/hexanes) provided methyl (8-acetylquinolin-2-yl)(phenyl)carbamate, which was used without further purification in the next step. m/z (ESI, +ve) 349.1 (M+H)+.

WORKUP

后处理

customPurification by column chromatography (silica gel: 0 to 10% EtOAc/hexanes followed by 70% EtOAc/hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c422b00f7ba54ddb9326e290bbbd8324
来源数据集: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09394297B2
来源说明: uspto-grants-2016_07

反应 SMILES

C([Sn](CCCC)(CCCC)[C:6]([O:8]CC)=[CH2:7])CCC.Br[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([N:30]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:31](=[O:34])[O:32][CH3:33])[CH:26]=[CH:25]2>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.C1(C)C=CC=CC=1>[C:6]([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([N:30]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:31](=[O:34])[O:32][CH3:33])[CH:26]=[CH:25]2)(=[O:8])[CH3:7]