氢化钠 → 6-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

HRID 245803

反应方程式

HRID 245803 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][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[CH:4][CH:3]=1

参与物

5

反应物 3

HCID 24758氢化钠HCID 27242712-(三甲基硅烷基)乙氧甲基氯HCID 178424716-溴吲唑

产物 1

HCID 673619576-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole收率 69%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
0 °C

实验过程

In a round-bottomed flask 6-bromo-1H-indazole (0.70 g, 3.55 mmol) was dissolved in DMF (7.5 ml). The reaction mixture was cooled to 0° C. and sodium hydride (60% dispersion in mineral oil, 172 mg, 4.3 mmol) was added). The reaction mixture was warmed to room temperature and stirred for 30 min then cooled back to 0° C. and SEM-Cl (0.76 ml, 4.28 mmol) was slowly added. After the addition was complete, the ice bath was removed and the reaction mixture was warmed to room temperature. After 1.5 h the reaction was quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/Hexanes (gradient 0-10% EtOAc) to give 802 mg (69%) of 6-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole as a light yellow oil.

后处理

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperaturethen cooled back to 0° C.
  3. additionAfter the addition
  4. customthe ice bath was removed
  5. temperaturethe reaction mixture was warmed to room temperature
  6. customAfter 1.5 h the reaction was quenched with water
  7. extractionextracted with diethyl ether (2×)
  8. washThe combined organic layers were washed twice with water and once with brine
  9. dry with materialthen dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was chromatographed over silica gel with EtOAc/Hexanes (gradient 0-10% EtOAc)

来源与证据

ORD记录
ord-31e08321afa54c9e94d4e7503a8b71a5
来源数据集
uspto-grants-2014_02
专利号
US08658646B2

关联笔记

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