Potassium Carbonate → Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]2-methylindol-4-carboxylate

HRID 52010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52010
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]([CH3:11])=[CH:5][C:4]=2[C:3]=1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[N:27]=[C:26](S(C)(=O)=O)[N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[N:27]=[C:26]([O:1][C:2]2[CH:10]=[CH:9][C:8]3[NH:7][C:6]([CH3:11])=[CH:5][C:4]=3[C:3]=2[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[N:25]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 19077266Benzyl 5-hydroxy-2-methylindol-4-carboxylate

Produkt 1

HCID 19962760Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]2-methylindol-4-carboxylateAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture comprising 2.2 g of benzyl 5-hydroxy-2-methylindol-4-carboxylate, 1.7 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.3 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at a temperature of from 70° to 80° C. for two hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.8 g (yield: 85%) of the desired product. mp: 135°-139° C.

Aufarbeitung

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe residue obtained by concentration under reduced pressure
  7. customwas crystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1f7760b0521044bf9540a7fb877206e6
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616537

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