苯甲酰氯 → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

HRID 609727笔记

反应方程式

HRID 609727 反应方程式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[NH3:16].[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:15]=[C:14]2[CH2:20][CH2:21][N:22]([CH3:23])[CH3:24]

参与物

7

反应物 3

HCID 7412苯甲酰氯HCID 8471三乙胺HCID 3602525-溴-N,N-二甲基乙胺基吲哚

产物 2

HCID 222氨收率 3%HCID 196004435-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole收率 167.3%

试剂、催化剂与溶剂 2

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 6344二氯甲烷溶剂2 次

实验过程

Benzoyl chloride (1.7 mL, 14.6 mmol) was added to a solution of 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (Example 3a, 9.5 mmol) in dichloromethane (70 mL) containing triethylamine (4 mL, 28.7 mmol) and DMAP (206 mg, 1.7 mmol). The resulting solution was stirred at room temperature for 20 h. Dilution with dichloromethane (500 mL) was followed by sequential washing with water (200 mL) and brine (150 mL), drying over sodium sulfate and removal of the solvent in vacuo. Flash chromatography (silica gel, 3-5% 2M methanolic ammonia in dichloromethane) yielded 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (2.95 g, 84%).

后处理

  1. washby sequential washing with water (200 mL) and brine (150 mL)
  2. dry with materialdrying over sodium sulfate and removal of the solvent in vacuo

来源与证据

ORD记录
ord-7797e7fb49944762b4a1c1951ca1d748
来源数据集
uspto-grants-1999_12
专利号
US05998438

反应笔记

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