HRID535418

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID4150924

9-benzyl-9-borabicyclo[3.3.1]nonane

C15H21B

结构：CC(C(=O)Nc1ccc(Br)c(C#Cc2ccccc2)n1)N(C)C(=O)OC(C)(C)C

HCID86694372

未命名化合物

PRODUCTS

生成物

结构：CC(C(=O)Nc1ccc(Cc2ccccc2)c(C#Cc2ccccc2)n1)N(C)C(=O)OC(C)(C)C

HCID86694407

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

结构：[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1

催化剂HCID635956

未命名化合物

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 70 °C

PROCEDURE

实验过程

A mixture of tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate C2a (50 mg, 0.11 mmol), 9-benzyl-9-borabicyclo[3.3.1]-nonane (283 μl, 0.14 mmol) Cs2CO3 (71 mg, 0.22 mmol), 1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (8.0 mg, 0.01 mmol) and dioxane (0.6 ml) is stirred under argon atmosphere for 45 minutes at 70° C. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 26 mg (51%). HPLC-MS: M+H=470; tR=1.97 min (*Method—4).

WORKUP

后处理

concentrationThe mixture is concentrated in vacuo
customthe product purified by RP HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-05f07892668a44938111e5d18600e475
来源数据集: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08859541B2
来源说明: uspto-grants-2014_10

反应 SMILES

[C:1]([O:5][C:6](=[O:29])[N:7]([CH:9]([CH3:28])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:30](B1C2CCCC1CCC2)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl.O1CCOCC1>[C:1]([O:5][C:6](=[O:29])[N:7]([CH:9]([CH3:28])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:15]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2]