Iodoethane → 1-Ethyl-2-methyl-6-nitro-1H-indole

HRID 2079914

Reaktionsgleichung

Reaktionsgleichung von HRID 2079914
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=2.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].I[CH2:25][CH3:26].C(OCC)(=O)C>CN(C=O)C>[CH2:25]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=2)[CH:10]=[C:2]1[CH3:1])[CH3:26]

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 6005082-Methyl-6-nitro-1H-indoleHCID 2724254Sodium bis(trimethylsilyl)amide

Produkt 1

HCID 574422751-Ethyl-2-methyl-6-nitro-1H-indoleAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Cool a solution of 2-methyl-6-nitro-1H-indole, 18 (0.31 g, 1.76 mmol) in anhydrous DMF (5 mL) under inert atmosphere at 0° C. Add sodium hexamethyldisilazide (1.0M in THF, 1.9 mL, 1.9 mmol) and stir 5 minutes. Add iodoethane (filtered through basic alumina) (0.43 mL, 5.28 mmol), warm to ambient temperature, and stir 2 hours. Quench the reaction with saturated aqueous sodium bicarbonate, add ethyl acetate, and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous brine. Dry the organic layer over sodium sulfate, filter, and concentrate in vacuo. Chromatograph over silica gel using hexanes/ethyl acetate (9:1) to afford the title compound, (0.36 g, 100%). 1H NMR (CDCl3, 300 MHz) δ 2.47 (s, 31), 4.18 (q, J=7.1 Hz, 2), 6.23 (s, 3H), 7.48 (d, J=8.8 Hz, 1H), 7.95 (dd, J=1.9, 8.6 Hz, 1H), 8.23 (d, J=1.9 Hz, 1H).

Aufarbeitung

  1. customQuench
  2. customthe reaction with saturated aqueous sodium bicarbonate
  3. washwash with saturated aqueous sodium bicarbonate
  4. dry with materialDry the organic layer over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8c02373d2b1848c2b67e6759d8ead9b2
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932284B2

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