HRID1695725

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：[CH3][Sn]([CH3])([CH3])[c]1cc(N)c2cnn(S(=O)(=O)c3ccccc3)c2c1

HCID58255743

未命名化合物

HCID59860141

N-(5-Bromo-2-methoxypyridin-3-yl)methanesulfonamide

C7H9BrN2O3S

PRODUCTS

生成物

结构：COc1ncc(-c2cc(N)c3cnn(S(=O)(=O)c4ccccc4)c3c2)cc1NS(C)(=O)=O

HCID66911247

未命名化合物

收率 52.4%

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HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 120 °C

PROCEDURE

实验过程

1-(Phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (4.2 g, 9.63 mmol), N-[5-bromo-2-(methyloxy)-3-pyridinyl]methanesulfonamide (3.25 g, 11.56 mmol) and Pd(PPh3)4 (1.113 g, 0.963 mmol) were weighed into a round-bottomed flask. DMF (30 ml) was added and the reaction was heated at 120° C. for 20 mins. The solvent was removed in vacuo and the crude material (9.8 g) was dissolved in DCM and loaded onto the top of a 750 g RediSep silica cartridge that was then eluted with 0-100% EtOAc/cyclohexane over 10 column volumes using the Companion XL. The product-containing fractions were combined and the solvent removed in vacuo to afford the title compound as a pale yellow solid (2.39 g).

WORKUP

后处理

customThe solvent was removed in vacuo
dissolutionthe crude material (9.8 g) was dissolved in DCM
washwas then eluted with 0-100% EtOAc/cyclohexane over 10 column volumes
customthe solvent removed in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-374961ca9721417f8da787916abe6d8e
来源数据集: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08163743B2
来源说明: uspto-grants-2012_04

反应 SMILES

[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16]([Sn](C)(C)C)[CH:15]=[C:14]([NH2:23])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:25]1[CH:26]=[C:27]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:28]([O:31][CH3:32])=[N:29][CH:30]=1>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.CN(C=O)C>[NH2:23][C:14]1[CH:15]=[C:16]([C:25]2[CH:26]=[C:27]([NH:33][S:34]([CH3:37])(=[O:35])=[O:36])[C:28]([O:31][CH3:32])=[N:29][CH:30]=2)[CH:17]=[C:18]2[C:13]=1[CH:12]=[N:11][N:10]2[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]