Potassium Carbonate → 1-ethyl-6-methoxy-2-[4-(2-methoxyethoxy)-phenyl]-1H-indole-3-carbonitrile

HRID 907159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907159
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:29][O:30][CH2:31][CH2:32]Br>CN(C=O)C>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:32][CH2:31][O:30][CH3:29])=[CH:20][CH:21]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 594253351-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile

Produkt 1

HCID 594260301-ethyl-6-methoxy-2-[4-(2-methoxyethoxy)-phenyl]-1H-indole-3-carbonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Ethyl-2-(4-hydroxy-phenyl)-6-methoxy-1H-indole-3-carbonitrile (40 mg, 0.14 mmol), prepared as in example 1Ga step B, was combined with K2CO3 (77 mg, 0.56 mmol), bromoethyl methyl ether (26 μL, 0.28 mmol), and DMF (450 μL). This was stirred at room temperature for 1 hour, and then at 75° C. for 3 hours. The reaction mixture was then partitioned between H2O and EtOAc. The organic layer was dried and concentrated. Purification by silica gel chromatography (CH2Cl2, 0-5% EtOAc) to yield 1-ethyl-6-methoxy-2-[4-(2-methoxyethoxy)-phenyl]-1H-indole-3-carbonitrile (44 mg, 90%) as a white solid.

Aufarbeitung

  1. waitat 75° C. for 3 hours
  2. customThe reaction mixture was then partitioned between H2O and EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (CH2Cl2, 0-5% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-220f9ee6196941ebb3c43b062ae6e062
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013006B2

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