N-溴代丁二酰亚胺(NBS) → 7-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

HRID 1815961

反应方程式

HRID 1815961 反应方程式
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@@H:7]([CH3:19])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH:11]=[N:10]1)([CH3:4])([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>C1COCC1>[Br:22][C:16]1[C:15]([OH:18])=[CH:14][CH:13]=[C:12]2[C:17]=1[N:9]([CH2:8][C@@H:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:21])[CH3:20])[CH3:19])[N:10]=[CH:11]2

参与物

5

反应物 3

HCID 67184N-溴代丁二酰亚胺(NBS)HCID 23665763亚硫酸氢钠HCID 1364116801-[(S)-2-(tert-Butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

产物 1

HCID 1364116817-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol收率 77%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

To a solution of the product from Step B (3.79 g, 12.4 mmol) in anhydrous THF (100 mL) at 0° C. was added N-bromosuccinimide (2.20 g, 12.4 mmol) in 3 portions over 10 min. After 20 min the mixture was poured into a saturated aqueous solution of sodium bisulfite (100 mL) and extracted with EtOAc (3×200 mL). The combined extracts were dried (MgSO4) and evaporated to a residue (4.79 g). Chromatography (silica, 10% EtOAc/hexane) gave a solid (3.66 g, 77%): mp 103-105° C.

后处理

  1. extractionextracted with EtOAc (3×200 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated to a residue (4.79 g)

来源与证据

ORD记录
ord-84a24f4e58d542c98312fd1bd110f047
来源数据集
uspto-grants-2005_04
专利号
US06881749B2

关联笔记

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