HRID1959406

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID11714598

(4-(N,N-Dimethylamino)phenyl)di-tert-butyl phosphine

C16H28NP

HCID66744469

未命名化合物

结构：CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(Br)nc1-c1nc2ccccc2n1C(=O)OC(C)(C)C

HCID86662069

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(C2=CCN(c3ccccc3)CC2)nc1-c1nc2ccccc2n1C(=O)OC(C)(C)C

HCID66745113

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID24290

未命名化合物

溶剂HCID962

Water

H2O

溶剂HCID1140

Toluene

C7H8

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

A mixture of tert-butyl 2-[3-[bis(tert-butoxycarbonyl)amino]-6-bromo-pyrazin-2-yl]benzimidazole-1-carboxylate (100 mg, 0.1694 mmol), 1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine (58 mg, 0.2034 mmol), 4-ditert-butylphosphanyl-N,N-dimethyl-aniline; dichloropalladium (2 mg, 0.002825 mmol) and K2CO3 (28 mg, 0.2026 mmol) in toluene (1000 μL) and water (120 μL) were heated to 100° C. overnight. The reaction was diluted with DCM, washed with water followed by 1M NaOH, dried (MgSO4) and concentrated in vacuo. The material was used crude in the next step (quantitative yield assumed).

WORKUP

后处理

washwashed with water
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4d50a4ca5ac244f4ab70a39989e5c70e
来源数据集: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08410112B2
来源说明: uspto-grants-2013_04

反应 SMILES

[C:1]([O:5][C:6]([N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:9]1[C:10]([C:16]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[N:17]=2)=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:39]1([N:45]2[CH2:50][CH:49]=[C:48](B3OC(C)(C)C(C)(C)O3)[CH2:47][CH2:46]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C(Cl)Cl.Cl[Pd]Cl>[C:1]([O:5][C:6]([N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:9]1[C:10]([C:16]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[N:17]=2)=[N:11][C:12]([C:48]2[CH2:49][CH2:50][N:45]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:46][CH:47]=2)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]