海萝胶 → 5-Bromo-pyridine-2-carboxylic acid (4-chloro-phenyl)-amide

HRID 1024190

反应方程式

HRID 1024190 反应方程式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.N1C=CC=CC=1.Cl>C(#N)C.CN(C)C1C=CN=CC=1.O>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:9])=[CH:14][CH:13]=1

参与物

8

反应物 4

HCID 313海萝胶HCID 1049吡啶HCID 78124-氯苯胺HCID 190907715-溴吡啶-2-甲酰氯

产物 1

HCID 595933715-Bromo-pyridine-2-carboxylic acid (4-chloro-phenyl)-amide

试剂、催化剂与溶剂 3

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6342乙腈溶剂

反应条件

温度
68 °C

实验过程

To 5-Bromo-pyridine-2-carbonyl chloride (69, 0.76 g, 3.4 mmol) in acetonitrile (29.0 mL) were added p-chloroaniline (53, 0.702 g, 5.50 mmol), 4-dimethylamino-pyridine (0.12 g, 0.96 mmol) and pyridine (2.9 mL, 0.036 mol). The reaction was stirred at 68° C. overnight, then poured into water, acidified with 1N HCl to pH around 1 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with dichloromethane to give a white solid (70, 0.75 g, 70.0%).

后处理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with dichloromethane
  7. customto give a white solid (70, 0.75 g, 70.0%)

来源与证据

ORD记录
ord-8d55364b25e644b4a76c53b27d8e02a8
来源数据集
uspto-grants-2014_05
专利号
US08722702B2

关联笔记

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