HRID81355

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

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

HCID58522554

未命名化合物

HCID58522567

未命名化合物

PRODUCTS

生成物

结构：COc1cc(C(=O)OCc2ccccc2)c(Cl)cc1Nc1ncc(Cl)c(Oc2cccc3c2C(=O)N(C)C3)n1

HCID58522534

Phenylmethyl 2-chloro-4-[[5-chloro-4-[(2,3-dihydro-2-methyl-3-oxo-1H-isoindol-4-yl)oxy]-2-pyrimidinyl]amino]-5-methoxybenzoate

C28H22Cl2N4O5

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HCID1140

Toluene

C7H8

溶剂HCID6342

Acetonitrile

C2H3N

溶剂HCID13387

N-Methyl-2-pyrrolidone

C5H9NO

CONDITIONS

反应条件

温度: 150 °C

PROCEDURE

实验过程

7-(2,5-dichloro-pyrimidin-4-yloxy)-2-methyl-2,3-dihydro-isoindol-1-one (0.10 g), benzyl 4-amino-2-chloro-5-methoxy-benzoate (0.28 g), Pd2dba3 (18 mg), X-Phos (37 mg) and Cs2CO3 are weighed into a microwave vial and argon flushing is carried out. Then toluene (1 mL) and NMP (50 μL) are added, argon flushing is carried out again and the mixture is stirred for 5 min at 150° C. in the microwave. For working up the mixture is diluted with ACN (20 mL) and combined with Isolute (Separtis GmbH). The solvent is eliminated in vacuo and then purified by preparative HPLC. (IC50=53 nmol)

WORKUP

后处理

custompurified by preparative HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-20943953e03d445aab920ef6e333b89c
来源数据集: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08846689B2
来源说明: uspto-grants-2014_09

反应 SMILES

Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:17]=2[C:16](=[O:18])[N:15]([CH3:19])[CH2:14]3)[C:5]([Cl:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[C:37]([O:38][CH3:39])=[CH:36][C:25]([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[C:24]([Cl:40])[CH:23]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.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].CN1C(=O)CCC1.C1(C)C=CC=CC=1>[Cl:40][C:24]1[CH:23]=[C:22]([NH:21][C:2]2[N:7]=[C:6]([O:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:17]=3[C:16](=[O:18])[N:15]([CH3:19])[CH2:14]4)[C:5]([Cl:20])=[CH:4][N:3]=2)[C:37]([O:38][CH3:39])=[CH:36][C:25]=1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27]