HRID531486

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(C#N)c3)c2)OC1(C)C

HCID71092746

未命名化合物

2 次

结构：Cc1ccc(S(=O)(=O)n2cc(I)c3cc(-c4cccc(NS(C)(=O)=O)c4)cnc32)cc1

HCID90030209

未命名化合物

2 次

PRODUCTS

生成物

结构：Cc1ccc(S(=O)(=O)n2cc(-c3cnn(Cc4cccc(C#N)c4)c3)c3cc(-c4cccc(NS(C)(=O)=O)c4)cnc32)cc1

HCID90031340

未命名化合物

收率 41.3%

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-ii of example-1, N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (Intermediate 9) (200 mg, 0.35 mmol) was coupled with 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile (Intermediate 14) (119.8 mg, 0.38 mmol) in sodium carbonate (111 mg, 1.05 mmol), PdCl2(dppf) (12.8 mg, 0.017 mmol) and DME/water (2/1 ml) to afford 90 mg (30% yield) of the pure product after column purification using 50% 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-f955b314fcd34dcea77a0f758a6eca07
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:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[N:4]([S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:3]=1.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[N:42][N:43]([CH2:45][C:46]3[CH:47]=[C:48]([CH:51]=[CH:52][CH:53]=3)[C:49]#[N:50])[CH:44]=2)O1.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>[C:49]([C:48]1[CH:47]=[C:46]([CH:53]=[CH:52][CH:51]=1)[CH2:45][N:43]1[CH:44]=[C:40]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=4)[CH:9]=3)[N:4]([S:22]([C:25]3[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH:3]=2)[CH:41]=[N:42]1)#[N:50]