碳酸钾 → 7-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-6-oxiranylmethoxy-1H-indazole

HRID 1815962

反应方程式

HRID 1815962 反应方程式
[Br:1][C:2]1[C:3]([OH:22])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH3:13])[N:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:29]([CH:31]1[O:33][CH2:32]1)Br>CC(C)=O>[Br:1][C:2]1[C:3]([O:22][CH2:29][CH:31]2[CH2:32][O:33]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])[CH3:13])[N:8]=[CH:7]2

参与物

5

反应物 3

HCID 11430碳酸钾HCID 18430环氧溴丙烷HCID 1364116817-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

产物 1

HCID 867596497-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-6-oxiranylmethoxy-1H-indazole收率 471.5%

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

实验过程

A suspension of the product from Step C (3.66 g, 9.51 mmol), potassium carbonate (1.92 g, 1.46 mmol), and epibromohydrine (1.32 mL, 1.60 mmol) in acetone (200 mL) was heated at reflux for 30 h. The solid was removed by filtration and the filtrate was concentrated to an oil that was purified by chromatography (silica, 2% to 10% EtOAc/hexane) to afford an oil (3.33 g, 79%): LC/MS (+APCI) m/z 441, 443 (M+H).

后处理

  1. temperaturewas heated
  2. temperatureat reflux for 30 h
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated to an oil that
  5. customwas purified by chromatography (silica, 2% to 10% EtOAc/hexane)

来源与证据

ORD记录
ord-ea57fbdc0e21441aa0466e4cc13e11a3
来源数据集
uspto-grants-2005_04
专利号
US06881749B2

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