HRID531480

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CC1(C)OB(c2cnn(Cc3cccc([N+](=O)[O-])c3)c2)OC1(C)C

HCID90030904

未命名化合物

2 次

结构：CC(C)(C)OC(=O)n1cc(I)c2cc(-c3cccc(NS(C)(=O)=O)c3)cnc21

HCID90031437

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)n1cc(-c2cnn(Cc3cccc([N+](=O)[O-])c3)c2)c2cc(-c3cccc(NS(C)(=O)=O)c3)cnc21

HCID118523971

未命名化合物

收率 68%

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

Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)

C34H28Cl2FeP2Pd

溶剂HCID18180031

未命名化合物

PROCEDURE

实验过程

Using similar reaction conditions as described in step-i of example 1, tert-butyl 3-iodo-5-(3-(methylsulfonamido)phenyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (intermediate-32) (300 mg, 0.5 mmol) was coupled with 1-(3-nitrobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 10) (211 mg, 0.6 mmol) in sodium carbonate (189 mg, 1.7 mmol), PdCl2(dppf) (20 mg, 0.02 mmol) and DME/water (3/3 ml) to afford 200 mg (59% yield) of the pure product after column purification using 30% ethyl acetate in hexane as eluent.

WORKUP

后处理

customreaction conditions

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c6c56c1d34504ac68dbf6489ef694ff2
来源数据集: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09353107B2
来源说明: uspto-grants-2016_05

反应 SMILES

I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:12]=3)[CH:9]=2)[N:4]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:3]=1.[N+:29]([C:32]1[CH:33]=[C:34]([CH:50]=[CH:51][CH:52]=1)[CH2:35][N:36]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[N:37]1)([O-:31])=[O:30].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.O>[CH3:21][S:18]([NH:17][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[C:10]3[C:2]([C:39]4[CH:38]=[N:37][N:36]([CH2:35][C:34]5[CH:50]=[CH:51][CH:52]=[C:32]([N+:29]([O-:31])=[O:30])[CH:33]=5)[CH:40]=4)=[CH:3][N:4]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:5]3=[N:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=1)(=[O:20])=[O:19]