HRID56723

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID46736817

[5-Chloro-2-(trifluoromethyl)phenyl]boronic acid

C7H5BClF3O2

结构：CC(C(=O)Nc1ccc(C(=O)OC(C)(C)C)cc1)n1cc(C#N)c(Br)cc1=O

HCID117622561

未命名化合物

PRODUCTS

生成物

结构：CC(C(=O)Nc1ccc(C(=O)OC(C)(C)C)cc1)n1cc(C#N)c(-c2cc(Cl)ccc2C(F)(F)F)cc1=O

HCID117622763

未命名化合物

PROCEDURE

实验过程

127 mg (purity 70%, 0.2 mmol) of tert-butyl 4-{[2-(4-bromo-5-cyano-2-oxopyridin-1(2H)-yl)propanoyl]amino}benzoate (racemate) and 54 mg (0.24 mmol) of 5-chloro-2-trifluoromethylphenylboronic acid in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct were reacted according to General Method 2A. After aqueous work-up, the crude product was triturated with water and the solid was filtered off, dried and purified further by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures). Yield: 124 mg (quant.)

WORKUP

后处理

customAfter aqueous work-up, the crude product was triturated with water
filtrationthe solid was filtered off
customdried
custompurified further by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e7c100ea53d64a1890d102735dd7566e
来源数据集: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09434690B2
来源说明: uspto-grants-2016_09

反应 SMILES

Br[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]([CH:10]([CH3:27])[C:11]([NH:13][C:14]2[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=2)=[O:12])[C:4](=[O:28])[CH:3]=1.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:39]([F:42])([F:41])[F:40])=[C:34](B(O)O)[CH:35]=1>>[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:39]([F:40])([F:41])[F:42])=[C:34]([C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]([CH:10]([CH3:27])[C:11]([NH:13][C:14]3[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=3)=[O:12])[C:4](=[O:28])[CH:3]=2)[CH:35]=1