HRID2301672

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID237573

methyl 4-sulfanylbenzoate

C8H8O2S

结构：CC(C)(C)[Si](C)(C)OCc1c(CCBr)c2cc(Cl)ccc2n1C(c1ccccc1)c1ccccc1

HCID70160579

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1ccc(SCCc2c(CO[Si](C)(C)C(C)(C)C)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1

HCID70160847

未命名化合物

收率 81%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

1-benzhydryl-3-(2-bromoethyl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indole (1 eq) was mixed with Methyl 4-mercaptobenzoate (2 eq) and KC2CO3 (1.9 eq) in DMF (0.09M). The resulting mixture was stirred at rt under N2 overnight. Water was then added, followed by regular work-up (eg. EtOAc extration, brine wash, etc) and column purification (1:6 EtOAc/Hexane as eluent) to give methyl 4-({2-[1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl]ethyl}sulfanyl)benzoate (yellow oil) in 81% yield.

WORKUP

后处理

washfollowed by regular work-up (eg. EtOAc extration, brine wash, etc) and column purification (1:6 EtOAc/Hexane as eluent)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3e55cba812464f8ebbb6230b40430770
来源数据集: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06500853B1
来源说明: uspto-grants-2002_12

反应 SMILES

[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25]Br)=[C:15]1[CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:36][C:37]1[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=1.O>CN(C=O)C>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][S:36][C:37]2[CH:38]=[CH:39][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:45][CH:46]=2)=[C:15]1[CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1