氨 → 2-Amino-6-(1H-pyrazol-1-yl)pyridine

HRID 1908986笔记

反应方程式

HRID 1908986 反应方程式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:3]=1.O.[NH3:14]>>[NH2:14][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:3]=1

参与物

4

反应物 3

HCID 222氨2 次HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 70605292-溴-6-(1H-吡唑-1-基)吡啶

产物 1

HCID 665204692-Amino-6-(1H-pyrazol-1-yl)pyridine收率 81%

实验过程

To a mixture of 2-bromo-6-(1H-pyrazol-1-yl)pyridine (3.0 mmol, 669 mg) and Cu2O (0.01 mmol, 1.0 mg) in glycol in autoclave NH3 was feed. The reaction was maintained under 10 atm of NH3 at 110° C. for 24 h. After cooling to room temperature, water was added and the aqueous phase 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=6:1 as eluent) to afford a white solid (388 mg, 81% yield). 1H NMR (400 MHz, CDCl3, ppm): 8.44 (s, 1H), 7.69 (s, 1H), 7.53 (m, 1H), 7.28 (m, 1H), 6.42-6.37 (m, 2H), 4.49 (br, 2H). 13C NMR (100 MHz, CDCl3, ppm): 151.45, 142.72, 140.73, 139.91, 127.58, 125.25, 110.89, 108.23.

后处理

  1. extractionthe aqueous phase was extracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter solvent evaporation
  5. customthe crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=6:1 as eluent)

来源与证据

ORD记录
ord-4fa80ff0e1c7418bb04267cf989f3656
来源数据集
uspto-grants-2013_12
专利号
US08598351B2

反应笔记

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