HRID2078309

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID11430

Potassium Carbonate

CK2O3

HCID16217443

未命名化合物

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

PRODUCTS

生成物

结构：COC/C=C/c1ccc2c(c1)C(C)(C)C(=O)C(C(=O)NCC(=O)OC(C)(C)C)=C2O

HCID67099854

未命名化合物

收率 78.7%

AUXILIARIES

试剂、催化剂与溶剂

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

溶剂HCID8857

Ethyl acetate

C4H8O2

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

1,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (500 mg, 1178 μmol, see Example 53) was dissolved in 1,4-dioxane (11785 μL). 2M K2CO3 in water (2357 μL, 4714 μmol), Pd(Ph3P)4 (136 mg, 118 μmol), and (E)-2-(3-methoxyprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (300 μL, 1414 μmol) were added, and the reaction was stirred at 80° C. for 2 hours. The reaction mixture was cooled to ambient temperature, diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 50 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (385 mg) after flash chromatography. MS m/e=438 (M+Na)+.

WORKUP

后处理

temperatureThe reaction mixture was cooled to ambient temperature
additionadded to a separatory funnel
custompartitioned with NaHCO3 (saturated, aqueous)
washwashed 2 times with 50 mL of NaHCO3 (saturated, aqueous)
customseparated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-156d299dfd22409082816f611124bb9a
来源数据集: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07928139B2
来源说明: uspto-grants-2011_04

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.C([O-])([O-])=O.[K+].[K+].O.[CH3:34][O:35][CH2:36]/[CH:37]=[CH:38]/B1OC(C)(C)C(C)(C)O1>O1CCOCC1.CCOC(C)=O.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>[OH:26][C:6]1[C:5]2[C:10](=[CH:11][C:2](/[CH:38]=[CH:37]/[CH2:36][O:35][CH3:34])=[CH:3][CH:4]=2)[C:9]([CH3:13])([CH3:12])[C:8](=[O:14])[C:7]=1[C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])=[O:16]