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Phthalimide → 2-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione

HRID 353778
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HRID 353778 반응식
[CH3:1][C:2]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]=[CH:9]1)([CH3:7])[CH2:3][CH2:4][CH2:5]O.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50]1(=[O:60])[NH:54][C:53](=[O:55])[C:52]2=[CH:56][CH:57]=[CH:58][CH:59]=[C:51]12>C1COCC1>[CH3:1][C:2]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]=[CH:9]1)([CH3:7])[CH2:3][CH2:4][CH2:5][N:54]1[C:50](=[O:60])[C:51]2[C:52](=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:53]1=[O:55]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 235114074-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-ol

생성물 1

HCID 235114002-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione수율 66%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-ol (1 eq) in THF (20 mL) was added dropwise diethyl azodicarboxylate (1.1 eq), triphenyl phosphine (1.1 eq) and phtalimide (1.1 eq). The yellow solution was stirred at room temperature overnight and the solution was concentrated. The crude product was directly purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH and 0.1% TEA to yield 2-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione (66%). MH+(375).

후처리

  1. concentrationthe solution was concentrated
  2. customThe crude product was directly purified by flash chromatography

출처 및 근거

ORD 기록
ord-3d06fd0df1c24300ba3e19f032d3333a
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06756359B2

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