HRID2301669

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID236603

Bromodiphenylmethane

C13H11Br

反应SMILES：COC(=O)C(=O)c1c(CO[Si](C)(C)C(C)(C)C)[nH]c2ccc(Cl)cc12

HCID90772388

未命名化合物

PRODUCTS

产物

反应SMILES：COC(=O)C(=O)c1c(CO[Si](C)(C)C(C)(C)C)n(C(c2ccccc2)c2ccccc2)c2ccc(Cl)cc12

HCID86758767

未命名化合物

收率 60%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

Methyl [2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl](oxo)acetate (1 eq), Ph2CHBr (2 eq) and Cs2CO3 (1.5 eq) were mixed in dry acetonitrile (0.13M) under N2. The mixture was heated with stirring to reflux for 3 hrs. The reaction mixture was cooled to rt and filtered and solvent was removed. Resulting residue was purified using a column with 1:4Hexane/CH2Cl2 as eluent to give methyl [1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy }methyl)-5-chloro-1H-indol-3-yl](oxo)acetate (yellow-brown solid) in 60% yield.

WORKUP

后处理

temperatureThe mixture was heated
temperatureto reflux for 3 hrs
filtrationfiltered
customsolvent was removed
customResulting residue was purified

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-5d35a49db6e440a3a8f38399b8580ae9
来源数据集: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US06500853B1
来源说明: uspto-grants-2002_12

反应SMILES

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