HRID471438

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1

HCID2734217

2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl

C26H36NP

结构：Cc1cc(O[Si](C)(C)C(C)(C)C)cc(C)c1B(O)O

HCID59838332

未命名化合物

结构：CCOC(=O)[C@H]1C[C@@H]1c1ccc(O[C@@H]2CCc3c2ccc(C#N)c3Br)cc1

HCID86703879

未命名化合物

2 次

PRODUCTS

生成物

结构：CCOC(=O)[C@H]1C[C@@H]1c1ccc(O[C@@H]2CCc3c2ccc(C#N)c3-c2c(C)cc(O[Si](C)(C)C(C)(C)C)cc2C)cc1

HCID86703878

未命名化合物

收率 62.3%

AUXILIARIES

试剂、催化剂与溶剂

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HCID962

Water

H2O

溶剂HCID1140

Toluene

C7H8

CONDITIONS

反应条件

温度: 110 °C

PROCEDURE

实验过程

Under nitrogen atmosphere, (1S,2S)-2-[4-((R)-4-Bromo-5-cyano-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester (Intermediate 13, 590 mg, 1.38 mmol), (4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)boronic acid (0.78 g, 2.77 mmol, WO2005/63729A1), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (54 mg, 0.138 mmol), tris(dibenzylideneacetone)dipalladium(0) (63.37 mg, 0.07 mmol) and sodium carbonate (500 mg, 4.71 mmol) are suspended in 10 mL of toluene and 5 mL of water. The reaction mixture is stirred at 110° C. for 12 h then it is concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 100/01 4 80/20) to give the title compound (Yield: 500 mg).

WORKUP

后处理

concentrationit is concentrated under vacuum
customThe crude product obtained
customis purified by flash chromatography (cyclohexane/ethyl acetate 100/01 4 80/20)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0f0686db68304ac185db5084c647a974
来源数据集: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08633182B2
来源说明: uspto-grants-2014_01

反应 SMILES

[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20](Br)[C:21]([C:25]#[N:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[Si:28]([O:35][C:36]1[CH:41]=[C:40]([CH3:42])[C:39](B(O)O)=[C:38]([CH3:46])[CH:37]=1)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.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]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([C:39]4[C:40]([CH3:42])=[CH:41][C:36]([O:35][Si:28]([C:31]([CH3:33])([CH3:32])[CH3:34])([CH3:30])[CH3:29])=[CH:37][C:38]=4[CH3:46])[C:21]([C:25]#[N:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2]