Carbonic acid sodium salt (1:2) → HCID 86671496，化合物

HRID 536627

反应方程式

HRID 536627 反应方程式
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][C:3]=1[CH:8]=[O:9].[CH3:10][C:11]1[CH:12]=[C:13]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:14]=[CH:15][C:16]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[Br:7][C:6]1[C:2]([C:16]2[CH:15]=[CH:14][C:13]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:12][C:11]=2[CH3:10])=[C:3]([CH:8]=[O:9])[S:4][CH:5]=1

参与物

6

反应物 3

HCID 10340Carbonic acid sodium salt (1:2)HCID 125595283,4-二溴噻吩-2-羧醛HCID 66715578HCID 66715578，化合物

产物 1

HCID 86671496HCID 86671496，化合物收率 323.9%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8071乙二醇二甲醚溶剂

反应条件

温度
100 °C

实验过程

To the solution of Intermediate 1 (4 g, 15 mmol) in a mixture of DME and H2O (150 mL/50 mL) were added N-(3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (3.6 g, 1.65 mmol) and Na2CO3 (2.8 g, 3.1 mmol), the mixture was degassed with N2, and Pd(PPh3)4 (500 mg) was added, then the mixture was heated to 100° C. under N2 overnight. The reaction solution was concentrated to remove the organic solution, then the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, concentrated under reduced pressure, the residue was purified by column chromatography to give N-(4-(4-bromo-2-formylthiophen-3-yl)-3-methylphenyl)methanesulfonamide (2.0 g, yield 35.7%).

后处理

  1. customthe mixture was degassed with N2, and Pd(PPh3)4 (500 mg)
  2. additionwas added
  3. concentrationThe reaction solution was concentrated
  4. customto remove the organic solution
  5. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by column chromatography

来源与证据

ORD记录
ord-1494e7372e5247a1b3caa74ff144e352
来源数据集
uspto-grants-2014_10
专利号
US08859611B2

关联笔记

加载中…