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

HRID 609727

반응식

HRID 609727 반응식
[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]

참가 물질

7

반응물 3

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

생성물 2

HCID 222Ammonia수율 3%HCID 196004435-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole수율 167.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-7797e7fb49944762b4a1c1951ca1d748
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998438

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