Hexane → 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole

HRID 3354

Reaktionsgleichung

Reaktionsgleichung von HRID 3354
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:12])[NH:7]2.[H-].[Na+].CCCCCC.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CN(C=O)C.O>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=3)[CH:5]=[C:6]2[CH3:12])=[CH:24][CH:23]=1

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indole

Produkt 1

HCID 108258491-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indoleAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

4-Methoxy-2-methyl-1H-indole (805 mg, 5 mmol) was added to a mixture of 200 mg (5 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 10 mL of DMF and after stirring for 0.5 hours, 0.6 mL (5 mmol) of 4-fluorobenzyl chloride was added. The mixture was stirred at room temperature for 18 hours, diluted with water-and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and after concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.1 g (84% yield) of 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole, melting at 104°-108° C.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationafter concentrating at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-69862c99df73480e9bc323a291044204
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733923

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