HRID327240

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID12417418

2-(Bromomethyl)quinoline

C10H8BrN

结构：COC(=O)C(C)(C)Cc1c(Cc2ccc(Cl)cc2)c2ccc(O)cc2n1C

HCID18947634

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C(C)(C)Cc1c(Cc2ccc(Cl)cc2)c2ccc(OCc3ccc4ccccc4n3)cc2n1C

HCID18947571

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

To a solution of 315 mg of the ester from Step B in 3 mL of DMF were added 225 mg of milled K2CO3 and 272 mg of 2-(bromomethyl)quinoline. The mixture was stirred at R.T. for 18 h, poured into 25% aq. NH4OAc, and extracted with ethyl acetate. The organic extract was dried over Na2SO4 and evaporated to dryness to give an oil which was chromatographed on flash silica gel using ethyl acetate:hexane (30:70) as eluant to give the title compound as a foam.

WORKUP

后处理

extractionextracted with ethyl acetate
extractionThe organic extract
dry with materialwas dried over Na2SO4
customevaporated to dryness
customto give an oil which
customwas chromatographed on flash silica gel

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-82814305347f4aec830fe0219adc07d2
来源数据集: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05272145
来源说明: uspto-grants-1993_12

反应 SMILES

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[C:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:3]1[CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23].C([O-])([O-])=O.[K+].[K+].Br[CH2:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:37]=1>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:35][C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=3)[CH:9]=2)[C:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:3]1[CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23]