HRID421969

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID66827

Boronic acid, phenyl-

C6H7BO2

结构：COC(=O)c1ccc2c(C3CCCCC3)c(Br)n(CC(=O)OC(C)(C)C)c2c1

HCID29943315

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1ccc2c(C3CCCCC3)c(-c3ccccc3)n(CC(=O)OC(C)(C)C)c2c1

HCID66674882

未命名化合物

收率 88%

AUXILIARIES

试剂、催化剂与溶剂

结构：Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1

催化剂HCID178418476

未命名化合物

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

To a solution of methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate in dioxane (0.06 M) was added bis(triphenylphosphine)palladium(II) dichloride (0.2 eq) at RT under a nitrogen atmosphere. Then aqueous Na2CO3 (2 M; 4 eq) followed by phenylboronic acid (2.5 eq) were added and the reaction was heated to 80° C. for 2 h. The reaction mixture was allowed to cool and concentrated in vacuo. DCM was added and the organic phase washed with H2O, brine and dried over Na2SO4 before being filtered and concentrated in vacuo. The crude material was purified by automated FC (SiO2; 95:5 EtOAc/PE) to afford the title compound (88%). (ES+) m/z 448 (M+H)+

WORKUP

后处理

additionwere added
temperatureto cool
concentrationconcentrated in vacuo
additionDCM was added
washthe organic phase washed with H2O, brine
dry with materialdried over Na2SO4
filtrationbefore being filtered
concentrationconcentrated in vacuo
customThe crude material was purified by automated FC (SiO2; 95:5 EtOAc/PE)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-daad0bfe27a64014854094917a9d18bd
来源数据集: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08101595B2
来源说明: uspto-grants-2012_01

反应 SMILES

Br[C:2]1[N:3]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.C([O-])([O-])=O.[Na+].[Na+].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:25]([O:24][C:22](=[O:23])[CH2:21][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([CH3:28])([CH3:27])[CH3:26]