Methyl iodide → [5-(1H-Indol-2-yl)-2-methoxy-phenyl]-methyl-amine

HRID 25516

Reaktionsgleichung

Reaktionsgleichung von HRID 25516
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH2:16])[CH:15]=1.[C:19](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH:16][CH3:19])[CH:15]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 99002045-(1H-indol-2-yl)-2-methoxy-phenylamine

Produkt 1

HCID 9921288[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-methyl-amineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In acetone (50 mL) was placed 5-(1H-indol-2-yl)-2-methoxy-phenylamine (2.38 g, 10 mmol). To this was added potassium carbonate (5.53 g, 40 mmol), and to the vigorously stirred mixture was added methyl iodide (1.55 g, 11 mmol). The mixture warmed to 40° C. and stirred for 48 hours. The mixture cooled to room temperature and was filtered free of inorganics. The resulting solution was evaporated in vacuo to give a solid which was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was separated, dried over magnesium sulfate, and evaporated in vacuo to give a tan solid. This solid was purified by flash chromatography over silica gel (5% ethyl acetate/methylene chloride). Evaporation of the appropriate fractions gave 0.68 g of pure compound. MS: M+1=253.1. 1H NMR (DMSO-d6) δ 2.79 (d, J=5.3 Hz, 3H), 3.80 (s, 3H), 5.08-5.12 (m, 1H), 6.69 (s, 1H), 6.83-7.05 (m, 5H), 7.33 (d, J=7.9 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 11.28 (s, 1H) ppm.

Aufarbeitung

  1. temperatureThe mixture cooled to room temperature
  2. filtrationwas filtered free of inorganics
  3. customThe resulting solution was evaporated in vacuo
  4. customto give a solid which
  5. customwas partitioned between ethyl acetate (50 mL) and water (50 mL)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a tan solid
  10. customThis solid was purified by flash chromatography over silica gel (5% ethyl acetate/methylene chloride)
  11. customEvaporation of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-5c508525b84f40e6abab25c56de6090c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858739B2

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