HRID1518254

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID795

Imidazole

C3H4N2

HCID139400

Triisopropylsilyl chloride

C9H21ClSi

结构：COC(=O)c1ccc2c(C3CCCCC3)c(-c3ccccc3CO)[nH]c2c1

HCID58677008

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1ccc2c(C3CCCCC3)c(-c3ccccc3CO[Si](C(C)C)(C(C)C)C(C)C)[nH]c2c1

HCID68701119

未命名化合物

收率 97%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

To an ice-cooled solution of methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate and imidazole (2 eq.) in DMF (0.4 M), chloro(triisopropyl)silane (2 eq.) was added dropwise. The mixture was stirred at RT for 7 h, diluted with EtOAc, washed with sat. aq. NH4Cl and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was subjected to flash chromatography (PE:EtOAc, 6:1). After evaporation of the solvents the product was obtained as colourless oil (97%). MS (ES−): 519.7 (M−H+).

WORKUP

后处理

additionwas added dropwise
washwashed with sat. aq. NH4Cl and brine
dry with materialThe organic phase was dried over Na2SO4
customevaporated in vacuo
customAfter evaporation of the solvents the product

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-31314d0f3ab44906a923aa4c8fa52c93
来源数据集: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08232390B2
来源说明: uspto-grants-2012_07

反应 SMILES

[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][OH:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CN=C1.Cl[Si:34]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36]>CN(C=O)C.CCOC(C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][O:27][Si:34]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1