HRID661347

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID74299

Benzeneboronic acid, p-chloro-

C6H6BClO2

结构：CCOC(=O)c1ccc(N2CCN(Cc3ccccc3Br)CC2)cc1

HCID16109102

Ethyl 4-{4-[(2-bromophenyl)methyl]piperazin-1-yl}benzoate

C20H23BrN2O2

PRODUCTS

生成物

结构：CCOC(=O)c1ccc(N2CCN(Cc3ccccc3-c3ccc(Cl)cc3)CC2)cc1

HCID16109105

未命名化合物

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HCID86587095

未命名化合物

PROCEDURE

实验过程

A mixture of EXAMPLE 2A (13.83 g), 4-chlorophenylboronic acid (7.04 g), bis(triphenylphosphine)palladium dichloride (481 mg) and 2M sodium carbonate (22.5 mL) in 7:3:2 DME/water/ethanol (200 mL) at 90° C. was stirred for 4.5 hours and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was flash chromatographed on silica gel with 5%-40% ethyl acetate/hexanes.

WORKUP

后处理

extractionextracted with ethyl acetate
dry with materialThe extract was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customchromatographed on silica gel with 5%-40% ethyl acetate/hexanes

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c87258aa11b346cb947d58b80ef49b96
来源数据集: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08084607B2
来源说明: uspto-grants-2011_12

反应 SMILES

Br[C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC.O.C(O)C>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=2[CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)=[CH:29][CH:28]=1