碘甲烷 → 6-溴-1-甲基吲唑

HRID 501271

反应方程式

HRID 501271 反应方程式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]I>C1COCC1>[CH3:13][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[CH:6]=[N:7]1.[CH3:13][N:7]1[CH:6]=[C:5]2[C:9]([CH:10]=[C:2]([Br:1])[CH:3]=[CH:4]2)=[N:8]1

参与物

6

反应物 3

HCID 6328碘甲烷HCID 24758氢化钠HCID 178424716-溴吲唑

产物 2

HCID 225586246-溴-2-甲基-2H-吲唑收率 43%HCID 225586756-溴-1-甲基吲唑收率 51%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

To 6-bromoindazole (402A) (5.0 g, 25.4 mmol) in THF (50 mL) was added sodium hydride (95%, 672 mg, 26.6 mmol) with ice bath cooling. The mixture was stirred for 30 minutes. Methyl iodide (6.36 mL, 102 mmol) was added at room temperature. The reaction mixture was quenched with ammonium chloride solution and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate and concentrated. Purification by column chromatography (SiO2, ethyl acetate/hexane gradient) afforded 1-methyl-6-bromoindazole (402B) (2.71 g, 51%) as a yellow oil and 2-methyl-6-bromoindazole (402C) (2.28 g, 43%) as a yellow crystalline solid.

后处理

  1. temperaturecooling
  2. customThe reaction mixture was quenched with ammonium chloride solution
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by column chromatography (SiO2, ethyl acetate/hexane gradient)

来源与证据

ORD记录
ord-11ee07161b1848069adbb6445ffc0db4
来源数据集
uspto-grants-2010_08
专利号
US07772263B2

关联笔记

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