Potassium Carbonate → HCID 178418739, Verbindung

HRID 11492

Reaktionsgleichung

Reaktionsgleichung von HRID 11492
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH2:30][Cl:31]>CN(C=O)C>[Cl:31][CH2:30][CH2:29][CH2:28][CH2:27][O:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178418971HCID 178418971, Verbindung

Produkt 1

HCID 178418739HCID 178418739, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of 3-[(4-hydroxy-phenylamino)-methylene]-1,3-dihydro-indol-2-one (0.945 g, 3.75 mmol) in 20 mL DMF is treated with potassium carbonate (777 mg, 1.5 equiv.) and 1-bromo-4-chlorobutane (1.1 equiv.). The reaction mixture is heated to 40° C. for 3 h. The reaction mixture is partitioned between EtOAc and water. The organic layer is collected and washed sequentially with H2O (1×), saturated aqueous NaHCO3 solution (1×), and brine (1×). The organic phase is dried and concentrated to give a solid. The solid is triturated with MeOH and collected by filtration to give the named compound as yellow solid (600 mg, 47%).

Aufarbeitung

  1. customThe reaction mixture is partitioned between EtOAc and water
  2. customThe organic layer is collected
  3. washwashed sequentially with H2O (1×), saturated aqueous NaHCO3 solution (1×), and brine (1×)
  4. customThe organic phase is dried
  5. concentrationconcentrated
  6. customto give a solid
  7. customThe solid is triturated with MeOH
  8. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e59928bf063b45659a6ee618c58ae04a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098236B2

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