HRID1919165

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CN1CCN(c2ccc(Nc3cc(B4OC(C)(C)C(C)(C)O4)cn(C)c3=O)nc2)CC1

HCID58043764

未命名化合物

结构：CC(=O)OCc1c(Br)cc(F)cc1N1CCn2c(cc3c2C2CCC3C2)C1=O

HCID68096577

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OCc1c(-c2cc(Nc3ccc(N4CCN(C)CC4)cn3)c(=O)n(C)c2)cc(F)cc1N1CCn2c(cc3c2C2CCC3C2)C1=O

HCID68096615

未命名化合物

收率 33%

AUXILIARIES

试剂、催化剂与溶剂

结构：Cl[Pd]Cl.[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1

催化剂HCID178418228

未命名化合物

溶剂HCID8071

未命名化合物

CONDITIONS

反应条件

温度: 130 °C

PROCEDURE

实验过程

A microwave vial equipped with a magnetic stirrer was charged with (2-bromo-4-fluoro-6-{7-oxo-3,6-diazatetracyclo[9.2.1.02,10.03,8]tetradeca-2(10),8-dien-6-yl}phenyl)methyl acetate 334g (293 mg, 0.65 mmol), 1-methyl-5-(5-(4-methylpiperazin-1-yl)pyridine-2-ylamino)-6-oxo-1,6-dihydropyridin-3-ylboronic acid 197f (450 mg, 1.3 mmol), PdCl2(dppf) (54 mg, 0.065 mmol), 2.0 M Na2CO3 (2.0 equiv), and 1,2-dimethoxyethane (18 mL). After three cycles of vacuum/argon flash, the mixture was heated at 130° C. under microwave irradiation for 0.5 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified on flash column chromatography eluting with 10:1 dichloromethane/methanol to afford 340a as a brown solid (130 mg, 33%). LCMS: [M+H]+ 666

WORKUP

后处理

customA microwave vial equipped with a magnetic stirrer
filtrationIt was then filtered
customthe filtrate was evaporated in vacuo
customThe residue was purified on flash column chromatography
washeluting with 10:1 dichloromethane/methanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6c4b9b0719cd4ee39c4cbf415332b65b
来源数据集: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08618107B2
来源说明: uspto-grants-2013_12

反应 SMILES

[C:1]([O:4][CH2:5][C:6]1[C:11]([N:12]2[C:24](=[O:25])[C:23]3[N:15]([C:16]4[CH:17]5[CH2:26][CH:20]([C:21]=4[CH:22]=3)[CH2:19][CH2:18]5)[CH2:14][CH2:13]2)=[CH:10][C:9]([F:27])=[CH:8][C:7]=1Br)(=[O:3])[CH3:2].[CH3:29][N:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[C:32]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([N:52]3[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]3)=[CH:48][N:47]=2)[C:31]1=[O:59].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[C:1]([O:4][CH2:5][C:6]1[C:11]([N:12]2[C:24](=[O:25])[C:23]3[N:15]([C:16]4[CH:17]5[CH2:26][CH:20]([C:21]=4[CH:22]=3)[CH2:19][CH2:18]5)[CH2:14][CH2:13]2)=[CH:10][C:9]([F:27])=[CH:8][C:7]=1[C:34]1[CH:33]=[C:32]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([N:52]3[CH2:53][CH2:54][N:55]([CH3:58])[CH2:56][CH2:57]3)=[CH:48][N:47]=2)[C:31](=[O:59])[N:30]([CH3:29])[CH:35]=1)(=[O:3])[CH3:2]