碘化钾 → 2-氨基-3-碘-5-溴吡啶

HRID 60210

反应方程式

HRID 60210 反应方程式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[I:9]([O-])(=O)=O.[K+].[I-].[K+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]([NH2:8])=[N:6][CH:7]=1

参与物

6

反应物 3

HCID 4875碘化钾HCID 706222-氨基-5-溴吡啶HCID 23665710Potassium Iodate

产物 1

HCID 15165082-氨基-3-碘-5-溴吡啶收率 179.8%

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 1118四氧化硫溶剂

反应条件

温度
100 °C

实验过程

A stirred solution of 5-bromo-pyridin-2-ylamine (50 g, 289 mmol) in 2M sulfuric acid (500 mL) was treated portionwise with potassium iodate (30.8 g, 144 mmol) and the mixture heated to 100° C. A solution of potassium iodide (26.5 g, 160 mmol) in water (50 mL) was added dropwise over ca. 1 hour. The mixture was allowed to stir for a further 30 minutes then cooled to ambient temperature. The pH of the aqueous phase was adjusted to 8-9 and the mixture extracted with ethyl acetate (×3). The combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine, dried (Na2SO4) and evaporated to afford the title compound as a brown solid (77.4 g, 90%). 1H NMR (300 MHz, CDCl3): 8.06 (d, J=2.2 Hz, 1H), 7.96 (d, J=2.2 Hz, 1H), 4.96 (s, 2H).

后处理

  1. temperaturethen cooled to ambient temperature
  2. extractionthe mixture extracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

来源与证据

ORD记录
ord-4568b1b4cc8942c8a9b06a4d9f8ea174
来源数据集
uspto-grants-2016_09
专利号
US09440976B2

关联笔记

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