HRID2216036

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID702

Ethanol

C2H6O

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID15887404

未命名化合物

结构：CSc1sc(C(N)=O)cc1S(=O)(=O)c1cnc(N)c(Br)c1

HCID21057129

未命名化合物

PRODUCTS

生成物

结构：CSc1sc(C(N)=O)cc1S(=O)(=O)c1cnc(N)c(-c2ccccc2C)c1

HCID21057130

未命名化合物

收率 32%

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

The procedure as in Example 1: step c was followed using 4-(6-amino-5-bromo-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide (25 mg, 0.06 mmol, Example 120: step a), o-tolyl phenyl boronic acid (33 mg, 0.25 mmol), Pd(PPh3)4 (14 mg, 0.01 mmol), aqueous Na2CO3 (2M, 0.4 mL), ethanol (0.4 mL) and toluene (0.8 mL). Purification by preparative SiO2 chromatography (25% EtOAc in hexanes) of the residue yielded the title compound (7.4 mg, 32%) as a brown solid. ESI-MS (m/z): Calcd. for C18H17N3O3S3: 420.0 (M+H); found: 420.2.

WORKUP

后处理

customPurification by preparative SiO2 chromatography (25% EtOAc in hexanes) of the residue

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0ea340c0aecf4cf6aa27c46c31488edf
来源数据集: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07109354B2
来源说明: uspto-grants-2006_09

反应 SMILES

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]([C:18]([NH2:20])=[O:19])[S:14][C:15]=2[S:16][CH3:17])(=[O:10])=[O:9])=[CH:4][C:3]=1Br.[C:22]1([CH3:37])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1C1C=CC=CC=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]([C:18]([NH2:20])=[O:19])[S:14][C:15]=2[S:16][CH3:17])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH3:37]