HRID2386788

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID10796

Cesium carbonate

CCs2O3

HCID2773342

[4-(Cyanomethyl)phenyl]boronic acid

C8H8BNO2

HCID67545637

未命名化合物

PRODUCTS

产物

HCID66697345

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID178418228

Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)

C34H28Cl2FeP2Pd

溶剂HCID284

Formic acid

CH2O2

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

A mixture of 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (Example 73 step 6, 40 mg), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (10 mg), Cs2CO3 (84 mg) and (4-cyanomethylphenyl)boronic acid (CAS Reg. No. 91983-26-5, 27 mg) in dioxane (1 ml) and water (0.1 ml) was heated at 80° C. for 20 min in a sealed tube. The mixture was acidified with HCOOH and then purified by prep. HPLC (C18-column, solvent gradient 30-98%) to give the title compound (27 mg). MS (m/e)=514.2 [M+H+].

WORKUP

后处理

custompurified by prep

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-a5ecf4bf2ccb4153aebe41c2986fa6ed
来源数据集: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US08268820B2
来源说明: uspto-grants-2012_09

反应SMILES

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:27])[C:9]([C:15]2[CH:26]=[CH:25][C:18]3[N:19]([CH3:24])[C:20](=[O:23])[N:21]([CH3:22])[C:17]=3[CH:16]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:28])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:35]([CH2:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1)#[N:36].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(O)=O>[Cl:28][C:4]1[CH:3]=[C:2]([C:41]2[CH:42]=[CH:43][C:38]([CH2:37][C:35]#[N:36])=[CH:39][CH:40]=2)[CH:7]=[CH:6][C:5]=1[CH:8]([CH3:27])[C:9]([C:15]1[CH:26]=[CH:25][C:18]2[N:19]([CH3:24])[C:20](=[O:23])[N:21]([CH3:22])[C:17]=2[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11]