HRID2079879

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID2783130

4-Cyano-3-fluorophenylboronic acid

C7H5BFNO2

结构：O=[N+]([O-])c1ccc2c(Br)cn(S(=O)(=O)c3ccccc3)c2c1

HCID57442196

未命名化合物

结构：N#Cc1ccc(-c2cn(S(=O)(=O)c3ccccc3)c3cc([N+](=O)[O-])ccc23)cc1F

HCID67101102

未命名化合物

PRODUCTS

生成物

结构：N#Cc1ccc(-c2c[nH]c3cc([N+](=O)[O-])ccc23)cc1F

HCID57442195

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

溶剂HCID962

Water

H2O

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

4-(1-Benzenesulfonyl-6-nitro-1H-indol-3-yl)-2-fluoro-benzonitrile from 1-benzenesulfonyl-3-bromo-6-nitro-1H-indole, 7, and 3-fluoro-4-cyanophenylboronic acid using Method AA: Pd2(dba)3, [(t-Bu3)PH]BF4, K2CO3, THF, H2O. Purify by precipitation from EtOAc/hexanes. Remove the benzenesulfonyl protecting group using TBAF and THF as described for 4-(6-nitro-1H-indol-3-yl)-benzonitrile (9) below. LRMS (API ES−)=280.0 (M−1).

WORKUP

后处理

customPurify by precipitation from EtOAc/hexanes
customRemove the benzenesulfonyl protecting group

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c55f1a02ecc442089933a62b63cec9f9
来源数据集: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07932284B2
来源说明: uspto-grants-2011_04

反应 SMILES

C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[C:12]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([F:30])[CH:23]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C1(S(N2C3C(=CC=C([N+]([O-])=O)C=3)C(Br)=C2)(=O)=O)C=CC=CC=1.FC1C=C(B(O)O)C=CC=1C#N.C([O-])([O-])=O.[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1COCC1>[F:30][C:24]1[CH:23]=[C:22]([C:12]2[C:13]3[C:18](=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[NH:10][CH:11]=2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]