碘 → 6-Chloro-2-iodopyridin-3-amine

HRID 513063

反应方程式

HRID 513063 反应方程式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[I:9]I>CCO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[Cl:1][C:2]1[N:7]=[C:6]([I:9])[C:5]([NH2:8])=[CH:4][CH:3]=1

参与物

5

反应物 2

HCID 807碘HCID 793052-氯-5-氨基吡啶

产物 1

HCID 184070436-Chloro-2-iodopyridin-3-amine收率 86.4%

试剂、催化剂与溶剂 2

HCID 159865硫酸银催化剂HCID 702乙醇溶剂

反应条件

温度
20 °C

实验过程

To a solution of 6-chloro-pyridin-3-ylamine (10.0 g, 77.8 mmol) in EtOH (150 mL) was added Ag2SO4 (12.1 g, 38.9 mmol) and I2 (23.7 g, 93.4 mmol) at room temperature. The mixture was stirred at 20° C. overnight. The solvent was removed by evaporation under vacuum. Water (100 mL) and EtOAc (200 mL) were added to the residue. The organic layer was separated and the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate 7:1) to give 6-chloro-2-iodo-pyridin-3-ylamine (17.1 g, 86%). 1H NMR (DMSO, 300 MHz) δ 7.16 (d, J=8.4 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 5.57 (s, 2H).

后处理

  1. customThe solvent was removed by evaporation under vacuum
  2. additionWater (100 mL) and EtOAc (200 mL) were added to the residue
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. customto give the crude product, which
  8. customwas purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate 7:1)

来源与证据

ORD记录
ord-df791a2e39074c7ca9e7896999ccfcac
来源数据集
uspto-grants-2015_08
专利号
US09102672B2

关联笔记

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