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Phenethyl bromide → Ethyl (2-phenethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate

HRID 2236112
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HRID 2236112 반응식
Cl.[CH2:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH2:5][CH2:4][NH:3]1.CCN(C(C)C)C(C)C.Br[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(#N)C>[CH2:31]([N:3]1[CH2:4][CH2:5][C:6]2[N:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[CH2:2]1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7666Phenethyl bromideHCID 81531DiisopropylethylamineHCID 71552668Ethyl (1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate hydrochloride

생성물 1

HCID 86614347Ethyl (2-phenethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate수율 60%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Step a): To a stirred solution of Intermediate 1 (50 mg, 0.17 mmol) and DIEA (73 μl, 0.42 mmol) in acetonitrile (1 ml) is added (2-bromo-ethyl)-benzene (26 μl, 0.19 mmol). The reaction mixture is stirred at rt overnight. The solvent is removed under reduced pressure and the crude product is purified by silica gel column chromatography (hexane/EtOAc 3:1, 1% NEt3), affording pure ethyl (2-phenethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate (37 mg) in 60% yield: tR (LC-2) 1.69 min; ESI-MS (pos. ion): m/z 363.26 [M+H]+ (calcd 362.46 for C23H26N2O2).

후처리

  1. customThe solvent is removed under reduced pressure
  2. customthe crude product is purified by silica gel column chromatography (hexane/EtOAc 3:1, 1% NEt3)

출처 및 근거

ORD 기록
ord-d215e2c42d424133862cfafa7d3afb6b
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714132B2

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