2-吡啶甲酸 → Ethyl 2-(5-chloropyridin-2-YL)acetate

HRID 82175

反应方程式

HRID 82175 反应方程式
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][N:9]=1.C(OCC)(=O)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].N1C=CC=CC=1C(O)=O>O1CCOCC1.[Cu-]=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:9][CH:10]=1

参与物

7

反应物 4

HCID 10182-吡啶甲酸HCID 7761丙二酸二乙酯HCID 10796碳酸氢铯HCID 8170982-溴-5-氯吡啶

产物 1

HCID 55263201Ethyl 2-(5-chloropyridin-2-YL)acetate收率 54%

试剂、催化剂与溶剂 2

HCID 178419072HCID 178419072，化合物催化剂HCID 312751,4-二氧六环溶剂

反应条件

温度
130 °C

实验过程

Cesium carbonate (71 g, 218 mmol) was added to 2-bromo-5-chloropyridine (14 g, 73 mmol) and diethyl malonate (22 mL, 145 mmol) in dry 1,4-dioxane (280 mL) and the solution was degassed with argon for 30 minutes. Then copper (I) oxide (2.8 g, 14.55 mmol) and picolinic acid (3.6 g, 29 mmol) were added and the mixture was stirred in a sealed vessel at 130° C. for 24 hours. The mixture was cooled to room temperature, quenched with water (100 mL) and extracted with EtOAc (3×100 ml). The organic extracts were washed with water (200 mL), brine (200 mL), dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc:Hexane 92:8) to afford the title compound as a yellow oil in 54% yield, 8.0 g.

后处理

  1. customthe solution was degassed with argon for 30 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. customquenched with water (100 mL)
  4. extractionextracted with EtOAc (3×100 ml)
  5. washThe organic extracts were washed with water (200 mL), brine (200 mL)
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (EtOAc:Hexane 92:8)

来源与证据

ORD记录
ord-81ff80f730b34595aaf541e143b1fa47
来源数据集
uspto-grants-2014_09
专利号
US08846698B2

关联笔记

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