HRID1868722

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC(C)(C)OC(=O)CNC(=O)C1=C(O)c2ccc(Br)cc2C(C)(C)C1=O

HCID67099764

未命名化合物

HCID178418260

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)CNC(=O)C1=C(O)c2ccc(C#N)cc2C(C)(C)C1=O

HCID67099761

未命名化合物

收率 60.2%

AUXILIARIES

试剂、催化剂与溶剂

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

催化剂HCID3014735

Tetraethylammonium cyanide

C9H20N2

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HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 75 °C

PROCEDURE

实验过程

1,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (310 mg, 731 μmol, see Example 53), dppf (162 mg, 292 μmol), tris(dibenzylideneacetone)dipalladium (66.9 mg, 73.1 μmol), copper cyanide (262 mg, 2923 μmol), and tetraethylammonium cyanide (126 mg, 804 μmol) were mixed in dioxane (6 mL) in a microwave tube under a nitrogen atmosphere. The reaction mixture was then stirred at 75° C. for 16 hours. The reaction mixture was returned to room temperature, fused to silica gel, and purified by silica flash chromatography (0-100% DCM/hexane) to give the desired ester as a white solid (163 mg). MS (m/e)=315.1 (M+H-tBu)+.

WORKUP

后处理

customwas returned to room temperature
custompurified by silica flash chromatography (0-100% DCM/hexane)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-446a6c1ad3f54af18f412f15c94e7d15
来源数据集: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07635715B2
来源说明: uspto-grants-2009_12

反应 SMILES

Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:26])=[C:7]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[C:8](=[O:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Cu](C#N)[C:28]#[N:29]>[C-]#N.C([N+](CC)(CC)CC)C.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.[Fe+2].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]>[C:28]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:26])=[C:7]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[C:8](=[O:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1)#[N:29]