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Acetonitrile → 7-[3-(2-Methyl-1H-indol-4-yloxy)-propyl]-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

HRID 40644
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인쇄 미리보기

반응식

HRID 40644 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([CH3:15])[NH:10]2.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[N:26]1[CH2:33][C@H:32]2[NH:34][CH2:35][C@@H:27]1[CH2:28][CH:29]=[CH:30][CH2:31]2.C([O-])([O-])=O.[K+].[K+].C(#N)C>O.C(OCC)(=O)C>[CH3:15][C:9]1[NH:10][C:11]2[C:7]([CH:8]=1)=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:34]1[CH2:35][CH:27]3[N:26]([C:17]4[CH:18]=[CH:19][C:20]5[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:16]=4)[CH2:33][CH:32]1[CH2:31][CH:30]=[CH:29][CH2:28]3)[CH:14]=[CH:13][CH:12]=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 59686818Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-eneHCID 692351584-(3-Chloro-propoxy)-2-methyl-1H-indole

생성물 1

HCID 692335407-[3-(2-Methyl-1H-indol-4-yloxy)-propyl]-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8857Ethyl Acetate용매

실험 절차

4-(3-Chloro-propoxy)-2-methyl-1H-indole (0.16 g, 0.72 mmol), Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (0.1 g, 0.38 mmol), K2CO3 (72 mg, 0.52 mmol), acetonitrile (30 mL) were placed in a round bottom flask and refluxed overnight. To the reaction mixture were then added ethyl acetate (100 mL) and water (100 mL) and the resulting mixture stirred for 30 minutes. The organic layer was separated and dried with magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield a crude solid. The crude solid was purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate] to yield the title compound as a residue.

후처리

  1. temperaturerefluxed overnight
  2. customThe organic layer was separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customto yield a crude solid
  7. customThe crude solid was purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate]

출처 및 근거

ORD 기록
ord-1c5d99f2cc2d4519bef9afd009cec41f
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530475B2

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