HRID723052

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

HCID21886096

3-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

C13H20BNO2

结构：CSc1sc(C(=N)NC(=O)OC(C)(C)C)cc1S(=O)(=O)c1cccc(Br)c1

HCID145857672

未命名化合物

PRODUCTS

生成物

结构：CSc1sc(C(=N)NC(=O)OC(C)(C)C)cc1S(=O)(=O)c1cccc(-c2c(C)cccc2N)c1

HCID145857623

未命名化合物

收率 28%

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 described in Example 1: step c was followed using 3-methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (95 mg. 0.41 mmol, Example 25: step b), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (100.7 mg, 0.21 mmol, Example 27: step c), Pd(PPh3)4 (47 mg, 0.04 mmol), aqueous Na2CO3 (2M, 0.8 mL, 1.6 mmol), ethanol (0.8 mL) and toluene (1.6 mL). Purification by preparative SiO2 TLC (33% EtOAc in hexanes) of the residue yielded the title compound (30 mg, 28%) as an off-white solid. ESI-MS (m/z): Calcd. For C24H27N3O4S3: 517.2; found: 517.8.

WORKUP

后处理

customPurification by preparative SiO2 TLC (33% EtOAc in hexanes) of the residue

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7c3048145f634ff9b8829d75ca68fecc
来源数据集: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07138530B2
来源说明: uspto-grants-2006_11

反应 SMILES

[CH3:1][C:2]1[C:3](B2OC(C)(C)C(C)(C)O2)=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[C:18]([O:22][C:23](=[O:44])[NH:24][C:25]([C:27]1[S:28][C:29]([S:42][CH3:43])=[C:30]([S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37](Br)[CH:36]=2)(=[O:34])=[O:33])[CH:31]=1)=[NH:26])([CH3:21])([CH3:20])[CH3:19].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>[C:18]([O:22][C:23](=[O:44])[NH:24][C:25]([C:27]1[S:28][C:29]([S:42][CH3:43])=[C:30]([S:32]([C:35]2[CH:36]=[C:37]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=3[NH2:8])[CH:38]=[CH:39][CH:40]=2)(=[O:34])=[O:33])[CH:31]=1)=[NH:26])([CH3:21])([CH3:20])[CH3:19]