HRID1868724

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)c2cc(Br)ccc2C(C)(C)C1=O

HCID67099310

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)c2cc(C#N)ccc2C(C)(C)C1=O

HCID67099651

未命名化合物

收率 49%

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-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate (297 mg, 700 μmol, prepared in Example 40A-D), dppf (155 mg, 280 μmol), tris(dibenzylideneacetone)dipalladium (64.1 mg, 70.0 μmol), copper cyanide (251 mg, 2800 μmol), and tetraethylammonium cyanide (120 mg, 770 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 5.5 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 an off-white solid (127 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-2227d2c487f4445389872b864912fe3c
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:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:5]2[OH:26].[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:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:5]2[OH:26])#[N:29]