乙醇 → 7-Bromo-2-ethylpyrazolo[1,5-a]pyridine-3-amine

HRID 347828笔记

反应方程式

HRID 347828 反应方程式
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:14][CH3:15])[C:10]([N+:11]([O-])=O)=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(O)C.O>[Zn].C(O)(=O)C>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:14][CH3:15])[C:10]([NH2:11])=[C:6]2[CH:5]=[CH:4][CH:3]=1

参与物

6

反应物 3

HCID 702乙醇HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 219844817-Bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridine

产物 1

HCID 210841117-Bromo-2-ethylpyrazolo[1,5-a]pyridine-3-amine收率 73.3%

试剂、催化剂与溶剂 2

HCID 23994Zinc催化剂HCID 176醋酸溶剂

反应条件

温度
65 °C

实验过程

To a suspension of 7-bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (1.78 g) in a mixed solution of ethanol (100 mL), water (50 mL) and acetic acid (10 mL) was added zinc powder (1.78 g) at room temperature and the reaction mixture was stirred for 1 hour at 65° C. The reaction mixture was filtered through celite to remove insoluble residue and the filtrate was evaporated under reduced pressure. Water was added to the obtained residue and extraction was performed with ethyl acetate, and after washing the organic extract with water, saturated aqueous sodium bicarbonate and brine, the organic extract was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (60 g) and the title compound (1.16 g) was obtained as a dark green oil from the ethyl acetate:n-hexane (4:1) fraction.

后处理

  1. filtrationThe reaction mixture was filtered through celite
  2. customto remove insoluble residue
  3. customthe filtrate was evaporated under reduced pressure
  4. additionWater was added to the obtained residue and extraction
  5. washafter washing the
  6. extractionorganic extract with water, saturated aqueous sodium bicarbonate and brine
  7. extractionthe organic extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (60 g)

来源与证据

ORD记录
ord-f7f28f656561437ea9b8e6ac9dac057a
来源数据集
uspto-grants-2007_02
专利号
US07176216B2

反应笔记

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