Diisopropylethylamine → 2-(4-Methoxy-phenyl)-N-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-yl]-acetamide

HRID 1263717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1263717
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39](Cl)=[O:40])=[CH:34][CH:33]=1>C1COCC1>[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39]([NH:1][C:2]2[CH:10]=[C:9]3[C:5](=[CH:4][CH:3]=2)[CH2:6][O:7][C:8]3=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[O:40])=[CH:34][CH:33]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 696591993-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 696597272-(4-Methoxy-phenyl)-N-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-yl]-acetamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(6-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (50.0 mg, 0.189 mmol) and N,N-diisopropylethylamine (98.8 μL, 0.567 mmol) in 2.0 mL THF was added 4-methoxyphenylacetyl chloride (28.9 μL, 0.189 mmol). After stirring at room temperature for 1 h, the slurry was warmed briefly, stirred 10 min at room temperature, filtered and rinsed with MeOH and EtOAc/hexanes (1:1) to afford the title compound (48.3 mg, 62%) as a yellow solid.

Aufarbeitung

  1. temperaturethe slurry was warmed briefly
  2. stirringstirred 10 min at room temperature
  3. filtrationfiltered
  4. washrinsed with MeOH and EtOAc/hexanes (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-67f2c80bdab94349adf6cbdbc720bde9
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541504B1

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