HRID877107

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID31268

Pyrrolidine

C4H9N

HCID2734682

(Triisopropylsilyl)acetylene

C11H22Si

结构：O=[N+]([O-])c1ccc(OCc2cccc(F)c2)c(Br)c1

HCID21874800

2-Bromo-1-[(3-fluorophenyl)methoxy]-4-nitrobenzene

C13H9BrFNO3

PRODUCTS

生成物

结构：CC(C)[Si](C#Cc1cc(N)ccc1OCc1cccc(F)c1)(C(C)C)C(C)C

HCID67504232

未命名化合物

结构：CC(C)[Si](C#Cc1cc([N+](=O)[O-])ccc1OCc1cccc(F)c1)(C(C)C)C(C)C

HCID67504616

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID24350

Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)

CuI

结构：Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1

催化剂HCID178418476

未命名化合物

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

To a solution of 1-((2-bromo-4-nitrophenoxy)methyl)-3-fluorobenzene (1 g), ethynyltriisopropylsilane (1.032 mL), pyrrolidine (0.3 mL) in DMF (20 mL) was added Pd(PPh3)2Cl2 (501 mg), CuI (117 mg) and the mixture was heated at 80° C. overnight. The solvent was removed, the residue was purified by flash chromatography, eluting with 10% EtOAc in hexane to give the desired product (2-(2-(3-fluorobenzyloxy)-5-nitrophenyl)ethynyl)triisopropylsilane (compound 23.1, 472 mg) and 4-(3-fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)benzenamine (compound 23.2, 440 mg). LCMS ESI(+) m/z: 428 (M+1) and LCMS ESI(+) m/z: 398 (M+1).

WORKUP

后处理

customThe solvent was removed
customthe residue was purified by flash chromatography
washeluting with 10% EtOAc in hexane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-bb93d7f4e3504348a5942ac9dd67077c
来源数据集: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08987284B2
来源说明: uspto-grants-2015_03

反应 SMILES

Br[C:2]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1.[C:20]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])#[CH:21].N1CCCC1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH2:5][O:4][C:3]1[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:2]=1[C:21]#[C:20][Si:22]([CH:23]([CH3:25])[CH3:24])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27].[F:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH2:5][O:4][C:3]1[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:2]=1[C:21]#[C:20][Si:22]([CH:23]([CH3:25])[CH3:24])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27]