HRID1529220

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID62657

Tripotassium phosphate

K3O4P

结构：CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1

HCID11155794

2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

C33H49P

HCID17750256

[3-Methoxy-4-(methoxycarbonyl)phenyl]boronic acid

C9H11BO5

HCID58235313

未命名化合物

PRODUCTS

生成物

结构：CCc1nccc(-c2ccc(C(=O)OC)c(OC)c2)c1C#Cc1ccc(N)nc1

HCID58235311

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

The title compound is synthesized according to general procedure GP3 starting from 1.5 g (5.0 mmol) 5-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-pyridin-2-ylamine (A-30) using 1.6 g (7.4 mmol) 3-methoxy-4-methoxycarbonylphenyl boronic acid, 135 mg (0.15 mmol) Pd2(dba)3, 354 mg (0.74 mmol) X-Phos and 2.2 g (9.4 mmol) K3PO4 in 20 mL dioxane. The reaction mixture is stirred under reflux over night. The solvent is removed under reduced pressure before water is added and the formed precipitate is collected by filtration. The product is purified by chromatography on silica gel using a DCM/MeOH-gradient. Yield: 1.07 g (56%).

WORKUP

后处理

temperatureunder reflux over night
customThe solvent is removed under reduced pressure before water
additionis added
filtrationthe formed precipitate is collected by filtration
customThe product is purified by chromatography on silica gel using a DCM/MeOH-gradient

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cd6ba0b87096456d83731071af1c7d4e
来源数据集: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09090564B2
来源说明: uspto-grants-2015_07

反应 SMILES

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=1[C:10]#[C:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[C:27]([O:29][CH3:30])=[O:28].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:25]=[CH:24][C:23]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=2[C:10]#[C:11][C:12]2[CH:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[CH:22][C:21]=1[O:20][CH3:19]