Benzoyl chloride → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

HRID 609727

反応式

HRID 609727 の反応式
[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]

参加物

7

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 3602525-Bromo-N,N-Dimethyltryptamine

生成物 2

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7797e7fb49944762b4a1c1951ca1d748
出典データセット
uspto-grants-1999_12
特許番号
US05998438

関連ノート

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