HRID1518224

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID292189

2-Formylphenylboronic acid

C7H7BO3

结构：COC(=O)c1ccc2c(C3CCCCC3)c(Br)n(CC(C(=O)OC)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c2c1

HCID68699898

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1ccc2c(C3CCCCC3)c(-c3ccccc3C=O)n(CC(C(=O)OC)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c2c1

HCID86637854

未命名化合物

收率 65%

AUXILIARIES

试剂、催化剂与溶剂

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HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

To a solution of methyl 1-{2-[bis(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}-2-bromo-3-cyclohexyl-1H-indole-6-carboxylate in dioxane (0.15 M) were added 6 eq of Na2CO3 (2 M aqueous solution), 1.5 eq (2-formylphenyl)boronic acid and 0.2 eq of bis(triphenylphosphine)palladium(II) dichloride. The mixture was heated at reflux for 1.5 h. The reaction mixture was filtered and then the filtrate was diluted with EtOAc. The organic phase was washed with H2O, brine and dried over Na2SO4 before being filtered and concentrated in vacuo. The crude was purified by flash chromatography (Biotage cartridge, 1.0:9.0 EtOAc/PE) to afford the title compound (65%). MS (ES+) m/z 663 (M+H)+.

WORKUP

后处理

temperatureThe mixture was heated
temperatureat reflux for 1.5 h
filtrationThe reaction mixture was filtered
additionthe filtrate was diluted with EtOAc
washThe organic phase was washed with H2O, brine
dry with materialdried over Na2SO4
filtrationbefore being filtered
concentrationconcentrated in vacuo
customThe crude was purified by flash chromatography (Biotage cartridge, 1.0:9.0 EtOAc/PE)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-523d33ae50b2474c8db494e429c9c06b
来源数据集: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08232390B2
来源说明: uspto-grants-2012_07

反应 SMILES

[C:1]([O:5][C:6]([N:8]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:9]([C:31]([O:33][CH3:34])=[O:32])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[C:13]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:12]1Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[CH:48]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1B(O)O)=[O:49]>O1CCOCC1.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>[C:1]([O:5][C:6]([N:8]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:9]([C:31]([O:33][CH3:34])=[O:32])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[C:13]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:12]1[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=1[CH:48]=[O:49])=[O:7])([CH3:4])([CH3:3])[CH3:2]