Methyl iodide → 2-Chloro-1-methyl-1H-indole-3-carbaldehyde

HRID 18296

Reaktionsgleichung

Reaktionsgleichung von HRID 18296
[H-].[Na+].[Cl:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.I[CH3:16]>CN(C=O)C>[Cl:3][C:4]1[N:5]([CH3:16])[C:6]2[C:11]([C:12]=1[CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3147912-chloro-1H-indole-3-carbaldehyde

Produkt 1

HCID 3147922-Chloro-1-methyl-1H-indole-3-carbaldehydeAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

NaH (60% dispersion in mineral oil) (0.9 g, 22.5 mmole) was added portionwise over 5 min to a solution of 2-chloro-1H-indole-3-carboxaldehyde (3.8 g, 21.2 mmole) and iodomethane (1.5 mL, 24 mmole) in DMF (50 mL) with stirring at 0° C. The reaction was allowed to warm to RT and stir for 4 h, then was concentrated under vacuum. The remaining residue was taken up in EtOAc, and the solution was washed with water then brine, dried (MgSO4), and concentrated to dryness. Trituration with 1:1 Et2O/petroleum ether, filtration, and drying under vacuum gave the title compound (3.10 g, 76%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1 H), 8.29 (m, 1 H), 7.33 (m, 3 H), 3.81 (s, 3 H); MS (ES) m/e 194.0 (M+H)+.

Aufarbeitung

  1. temperatureto warm to RT
  2. stirringstir for 4 h
  3. concentrationwas concentrated under vacuum
  4. washthe solution was washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. concentrationconcentrated to dryness
  7. filtrationTrituration with 1:1 Et2O/petroleum ether, filtration
  8. customdrying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-386933c6fe284709b89335c54cf72079
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741339B2

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