HRID1261904

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

HCID11430

Potassium Carbonate

CK2O3

HCID66827

Boronic acid, phenyl-

C6H7BO2

HCID574072

Trimethylboroxine

C3H9B3O3

结构：CSc1ncc2c(Br)cc(-c3ccc(S(C)(=O)=O)cc3)n2n1

HCID66711707

未命名化合物

PRODUCTS

生成物

结构：CSc1ncc2c(C)cc(-c3ccc(S(C)(=O)=O)cc3)n2n1

HCID66711473

未命名化合物

收率 65%

HCID66711707

未命名化合物

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

CONDITIONS

反应条件

温度: 130 °C

PROCEDURE

实验过程

Into a 30 mL vial, 5-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.480 g, 0.00120 mol) (Note: 5-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine was prepared in an analogous fashion as Example 99b replacing Phenylboronic acid with $-methylsulfonuphenylboronic acid), Trimethylboroxine (1.37 g, 0.0109 mol), Tetrakis(triphenylphosphine)palladium (0) (0.14 g, 0.00012 mol) and Potassium carbonate (7.49 g, 0.0542 mol) were added and purged under an atmosphere of Nitrogen for 10 minutes. N,N-Dimethylformamide (25.0 mL, 0.323 mol) was then added and heated at 130° C. for 4 hours. The reaction was partitioned with water and EtOAc. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The product was isolated via ISCO column chromatography with DCM and MeOH as eluant (0 to 5% MeOH). The collected fractions afforded 7-(4-Methanesulfonyl-phenyl)-5-methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (0.26 g, 65%).

WORKUP

后处理

additionwere added
custompurged under an atmosphere of Nitrogen for 10 minutes
customThe reaction was partitioned with water and EtOAc
customThe organic was separated
washwashed with Brine
dry with materialdried over magnesium sulfate
filtrationThe solid was filtered
washwashed with EtOAc
customThe solvent was removed under vacuum
customThe product was isolated via ISCO column chromatography with DCM and MeOH as eluant (0 to 5% MeOH)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f0adcd715bf64ffe9c07394549a1f97f
来源数据集: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08471005B2
来源说明: uspto-grants-2013_06

反应 SMILES

[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.[C:23]1(B(O)O)C=CC=CC=1.CB1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>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>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:4]2[N:5]3[C:10]([CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]3)=[C:2]([CH3:23])[CH:3]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]