HRID1714040

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8857

Ethyl acetate

C4H8O2

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID2773426

2-Formylthiophene-3-boronic acid

C5H5BO3S

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(-c3ccsc3C=O)n(CC(=O)OC(C)(C)C)c2c1

HCID86604968

未命名化合物

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

PROCEDURE

实验过程

Methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in Example 1, Step 1) and (2-formyl-3-thienyl) boronic acid (1.5 eq) were dissolved in dioxane (0.07 M) and 2M aqueous Na2CO3 (6 eq) was added. The solution was degassed by bubbling argon, Pd(PPh3)2Cl2 (0.2 eq) was added, and the reaction mixture was refluxed for 45 min; after cooling EtOAc was added and the solution washed with water and brine, dried over Na2SO4 and concentrated. The title compound was isolated by chromatography (PE/EtOAc 9:1). Yield (84%); MS (ES+) m/z 504 (M+Na)+.

WORKUP

后处理

customThe solution was degassed
additionwas added
temperaturethe reaction mixture was refluxed for 45 min
additionwas added
washthe solution washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f215ef09e56f4f488a04dfb2fe4ce3c5
来源数据集: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07795247B2
来源说明: uspto-grants-2010_09

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.[CH:29]([C:31]1[S:32][CH:33]=[CH:34][C:35]=1B(O)O)=[O:30].C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>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:34]=[CH:33][S:32][C:31]=1[CH:29]=[O:30])([CH3:28])([CH3:27])[CH3:26]