HRID723106

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID702

Ethanol

C2H6O

HCID1140

Toluene

C7H8

HCID428351

4-Bromo-3-methylpyridine

C6H6BrN

结构：Bc1c(O)ccc(S(=O)(=O)c2cc(C(=N)NC(=O)OC(C)(C)C)sc2SC)c1O

HCID178419158

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(-c2ccncc2C)c1

HCID145857644

未命名化合物

收率 410%

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HCID8857

Ethyl acetate

C4H8O2

溶剂HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

PROCEDURE

实验过程

4-Bromo-3-methyl-pyridine (100 mg, 0.219 mmol, Example 138: step b), {[4-(3-Boranyl-dihydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (266 mg, 0.58 mmol, Example 140: step a) and Pd(PPh3)4 (134 mg, 0.12 mmol) were combined in aqueous Na2CO3 (2M, 2 mL), ethanol (2 mL) and toluene (4 mL) and heated to 80° C. overnight. The reaction mixture was dissolved into EtOAc and washed with brine. The organic layers were dried (MgSO4) and the solvent was removed in vacuo. Purification by flash column chromatography (10% DCM/MeOH) afforded the title compound (120 mg, 410%). ESI-MS (m/z): Calcd. for C23H25N3O4S3: 504.1 (M+1); found: 503.7.

WORKUP

后处理

washwashed with brine
dry with materialThe organic layers were dried (MgSO4)
customthe solvent was removed in vacuo
customPurification by flash column chromatography (10% DCM/MeOH)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e7d646efbd4648e3b3ddc010c62c5278
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

Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH3:8].[C:9]([O:13][C:14](=[O:37])[NH:15][C:16]([C:18]1[S:19][C:20]([S:35][CH3:36])=[C:21]([S:23]([C:26]2[CH:31]=[CH:30][C:29](O)=[C:28](B)[C:27]=2O)(=[O:25])=[O:24])[CH:22]=1)=[NH:17])([CH3:12])([CH3:11])[CH3:10].C(O)C.C1(C)C=CC=CC=1>C([O-])([O-])=O.[Na+].[Na+].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.CCOC(C)=O>[C:9]([O:13][C:14](=[O:37])[NH:15][C:16](=[NH:17])[C:18]1[S:19][C:20]([S:35][CH3:36])=[C:21]([S:23]([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][C:3]=3[CH3:8])[CH:31]=2)(=[O:25])=[O:24])[CH:22]=1)([CH3:12])([CH3:10])[CH3:11]