HRID2359638

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

结构：COc1ccc(Oc2nc(Cl)ncc2NC[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1

HCID58243046

未命名化合物

PRODUCTS

生成物

结构：COc1ccc(Oc2nc(C#N)ncc2NC[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1

HCID58247356

未命名化合物

收率 15%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID11186

Zinc cyanide (Zn(CN)2)

C2N2Zn

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

PROCEDURE

实验过程

A mixture of Compound 1e (0.4 g; 0.92 mmol), Zn(CN)2 (0.11 g; 0.92 mmol), and Pd(PPh3)4 (0.106 g; 0.092 mmol) in DMF (2.4 mL) was irradiated at 160° C. in a CEM microwave reactor for 16 min. Purification by preparative TLC, eluting with 1/1 EtOAc/hexanes, gave the product 6a (0.059 g; 15% yield). MS: m/z 426.2 (M+H)+.

WORKUP

后处理

customwas irradiated at 160° C. in a CEM microwave reactor for 16 min
customPurification by preparative TLC
washeluting with 1/1 EtOAc/hexanes

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3510e914ea7342669b753d29d963c8e2
来源数据集: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08685990B2
来源说明: uspto-grants-2014_04

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15]1[C:16]([O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[N:17][C:18](Cl)=[N:19][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31][N:32](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15]1[C:16]([O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[N:17][C:18]([C:31]#[N:32])=[N:19][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]