HRID1473593

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID11534

Bromoacetonitrile

C2H2BrN

结构：COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(-c4ccccc4O)nccc3c2)cc1

HCID136409071

未命名化合物

PRODUCTS

生成物

结构：COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(-c4ccccc4OCC#N)nccc3c2)cc1

HCID86687656

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

To a vial charged with 1-(2-hydroxyphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (113 mg, 0.224 mmol) was added DMF (898 μl) and Cs2CO3 (219 mg, 0.673 mmol) and bromoacetonitrile (53.8 mg, 0.45 mmol) respectively. The mixture was heated to 60° C. overnight affording conversion to desired product fairly cleanly. m/z (ESI) 543.2 (M+H)+. The mixture was dried under reduced pressure and purified with a 25 g Interchim column (25 μm silica) ramping EtOAc in heptane (0-100%, 10% DCM throughout) affording product as a light brown solid. m/z (ESI) 543.2 (M+H)+

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-28265ecaf7ba4c9e87a85e47729a02b8
来源数据集: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09012443B2
来源说明: uspto-grants-2015_04

反应 SMILES

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([N:21]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:43][C:44]#[N:45]>CN(C=O)C>[C:44]([CH2:43][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([N:21]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1)#[N:45]