1-Chloromethylnaphthalene → 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole

HRID 566661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566661
[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+].Cl[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>CN(C=O)C.O>[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])[N:7]2[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indole

Produkt 1

HCID 106380394-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indoleAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Methoxy-2-methyl-1H-indole (644 mg, 4 mmol) was dissolved in 10 mL of DMF and 160 mg (4 mmol) of 60% NaH/mineral oil was added. After 0.67 hours, 707 mg (4 mmol) of 1-(chloromethyl)naphthalene was added. After 5 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 1.17 g (97% yield) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.

Aufarbeitung

  1. waitAfter 5 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined ethyl acetate was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluted with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-261344731524489ea0010801882962ac
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06175021B1

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