HRID274418

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID11430

Potassium Carbonate

CK2O3

HCID15171301

未命名化合物

结构：COC(=O)C(C)(C)Cc1c(C)c2cc(O)ccc2n1Cc1ccc(Cl)cc1

HCID15229448

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C(C)(C)Cc1c(C)c2cc(OCc3ccc(-c4ccccc4)cn3)ccc2n1Cc1ccc(Cl)cc1

HCID15229449

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A solution of methyl 3-[1-(4-chlorobenzyl)-3-methyl-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (180 mg) (Preparation 1), 5-phenyl-2-picolyl bromide (138 mg), K2CO3 (84 mg) and Cs2CO3 (30 mg) in DMF (5 mL) wase stirred at r.t. under nitrogen for 48 hours. The mixture was poured onto 1N HCL, extracted 2× EtOAc, washed 2× brine, dried (MgSO4), and evaporated to dryness. The residue was purified by column chromatography (hexane/EtOAc 5:1 then 1:1) to give the title compound.

WORKUP

后处理

additionThe mixture was poured onto 1N HCL
extractionextracted 2× EtOAc
washwashed 2× brine
dry with materialdried (MgSO4)
customevaporated to dryness
customThe residue was purified by column chromatography (hexane/EtOAc 5:1

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5a87c71a46ea426eb8635a9f01235f3b
来源数据集: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05389650
来源说明: uspto-grants-1995_02

反应 SMILES

[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([CH3:17])=[C:8]2[CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1.[C:28]1([C:34]2[CH:35]=[CH:36][C:37]([CH2:40]Br)=[N:38][CH:39]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:40][C:37]4[CH:36]=[CH:35][C:34]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)=[CH:39][N:38]=4)=[CH:13][CH:14]=3)[C:9]([CH3:17])=[C:8]2[CH2:18][C:19]([CH3:24])([CH3:25])[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1