HRID531515

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CS(=O)(=O)Nc1cccc(-c2cnc3[nH]cc(-c4cnn(Cc5ccccc5F)c4)c3c2)c1

HCID72944747

未命名化合物

结构：Cc1ccc(S(=O)(=O)n2cc(-c3c(C)nn(Cc4cccc(F)c4)c3C)c3cc(Br)cnc32)cc1

HCID90031306

未命名化合物

结构：CN(C)CCCOc1ccc(B2OC(C)(C)C(C)(C)O2)cc1NS(C)(=O)=O

HCID90031661

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(S(=O)(=O)n2cc(-c3c(C)nn(Cc4cccc(F)c4)c3C)c3cc(-c4ccc(OCCCN(C)C)c(NS(C)(=O)=O)c4)cnc32)cc1

HCID90030630

未命名化合物

收率 13.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID18180031

未命名化合物

PROCEDURE

实验过程

Using similar reaction conditions as described in step-ii of example 1, 5-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step-i of example-14) (250 mg, 0.4 mmol) was coupled with N-(2-(3-(dimethylamino)propoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (intermediate-30) (200 mg, 0.5 mmol) in sodium carbonate (154 mg, 1.4 mmol) PdCl2(dppf) (18 mg, 0.05 mmol), 1,2-dimethoxyethane/water (2/2 mL) to afford 40 mg (12% yield) of the titled compound after purification by preparative TLC (SiO2)-eluted by 30% ethyl acetate in hexane.

WORKUP

后处理

customreaction conditions

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-41aa28dadfdf47f68bbaa515dd809037
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

FC1C=CC=CC=1CN1C=C(C2C3C(=NC=C(C4C=C(NS(C)(=O)=O)C=CC=4)C=3)NC=2)C=N1.Br[C:35]1[CH:36]=[C:37]2[C:43]([C:44]3[C:45]([CH3:58])=[N:46][N:47]([CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[C:53]([F:57])[CH:52]=4)[C:48]=3[CH3:49])=[CH:42][N:41]([S:59]([C:62]3[CH:68]=[CH:67][C:65]([CH3:66])=[CH:64][CH:63]=3)(=[O:61])=[O:60])[C:38]2=[N:39][CH:40]=1.[CH3:69][N:70]([CH3:95])[CH2:71][CH2:72][CH2:73][O:74][C:75]1[CH:80]=[CH:79][C:78](B2OC(C)(C)C(C)(C)O2)=[CH:77][C:76]=1[NH:90][S:91]([CH3:94])(=[O:93])=[O:92].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH3:95][N:70]([CH3:69])[CH2:71][CH2:72][CH2:73][O:74][C:75]1[CH:80]=[CH:79][C:78]([C:35]2[CH:36]=[C:37]3[C:43]([C:44]4[C:45]([CH3:58])=[N:46][N:47]([CH2:50][C:51]5[CH:56]=[CH:55][CH:54]=[C:53]([F:57])[CH:52]=5)[C:48]=4[CH3:49])=[CH:42][N:41]([S:59]([C:62]4[CH:63]=[CH:64][C:65]([CH3:66])=[CH:67][CH:68]=4)(=[O:60])=[O:61])[C:38]3=[N:39][CH:40]=2)=[CH:77][C:76]=1[NH:90][S:91]([CH3:94])(=[O:93])=[O:92]