吡唑 → 2-溴-6-(1H-吡唑-1-基)吡啶

HRID 1908985笔记

反应方程式

HRID 1908985 反应方程式
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.CC([O-])(C)C.[K+].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[N:14]=1>O1CCOCC1>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[N:14]=1

参与物

5

反应物 3

HCID 1048吡唑HCID 122742,6-二溴吡啶HCID 23665647叔丁醇钾

产物 1

HCID 70605292-溴-6-(1H-吡唑-1-基)吡啶收率 90%

试剂、催化剂与溶剂 1

HCID 312751,4-二氧六环溶剂

实验过程

To a solution of 1H-Pyrazole (10.0 mmol, 680 mg) in distilled dioxane (30 mL) were added KOtBu (11.0 mmol, 1.26 g), and followed by addition of 2,6-dibromopyridine (10.0 mmol, 2.37 g). The reaction mixture was refluxed for 48 hour, and then quenched with 5 mL of water. Solvent was removed under reduced pressure and water was added to the residue, then the mixture was extracted with DCM. The combined organic layers were washed with brine and dried over MgSO4. After solvent evaporation, the crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=20:1 as eluent) to afford a white solid (2.01 g, 90%). 1H NMR (400 MHz, CDCl3, ppm): 8.53 (s, 1H), 7.92 (d, 1H, J=7.6 Hz), 7.73 (s, 1H), 7.67 (t, 1H, J=7.8 Hz), 7.35 (d, 1H, 7.6 Hz), 6.46 (s, 1H). 13C NMR (100 MHz, CDCl3, ppm): 162.72, 140.73, 139.91, 127.58, 125.25, 110.89, 108.23.

后处理

  1. temperatureThe reaction mixture was refluxed for 48 hour
  2. customquenched with 5 mL of water
  3. customSolvent was removed under reduced pressure and water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with DCM
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. customAfter solvent evaporation
  9. customthe crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=20:1 as eluent)

来源与证据

ORD记录
ord-95e63f97ec00497b9e4dd19c82b313a5
来源数据集
uspto-grants-2013_12
专利号
US08598351B2

反应笔记

加载中…