聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole

HRID 38547

反应方程式

HRID 38547 反应方程式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].Cl.Cl[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[N:8]=[CH:7]2)([O-:3])=[O:2]

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 11430碳酸钾HCID 215015-硝基吲唑HCID 23392Picolyl chloride hydrochloride

产物 1

HCID 224961495-nitro-1-(pyridin-2-ylmethyl)-1H-indazole收率 50.5%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

5-Nitroindazole (10.0 g, 61.3 mmol) was dissolved in THF (100 mL), and 2-(chloromethyl)pyridine hydrochloride (8.60 g, 52.4 mmol) and potassium carbonate (24.4 g, 184 mmol) were added. The mixture was heated for 4 h to 75° C. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate) to yield 6.73 g (43%) of the title compound.

后处理

  1. temperatureThe mixture was heated for 4 h to 75° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by column chromatography on silica gel (eluent: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate)

来源与证据

ORD记录
ord-91d9d9e2622743368ade6bd13677bb0a
来源数据集
uspto-grants-2013_09
专利号
US08524722B2

关联笔记

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