Methyl iodide → Ethyl 1,2-dimethyl-1H-indole-3-carboxylate

HRID 642416

Reaktionsgleichung

Reaktionsgleichung von HRID 642416
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH3:15])=[O:5])[CH3:2].[CH3:16]I.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH3:16])[C:7]=1[CH3:15])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4072358ethyl 2-methyl-1H-indole-3-carboxylate

Produkt 1

HCID 599139Ethyl 1,2-dimethyl-1H-indole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-water bath cooled solution of 2-methyl-1H-indole-3-carboxylic acid ethyl ester (5.197 g, prepared according to Suzuki et al. (1984) Synthesis (Stuttgart) 7:616-617), MeI (2.07 mL) in DMF (25 mL) was added NaH (1.33 g, 60% purity in mineral oil) under nitrogen gas stream. The reaction was stirred for 10 min at 0° C. and 20 min at room temperature and then quenched with diluted HCl solution, diluted with ice/water to a volume of ˜200 mL; the mixture was cooled with ice/water bath and the solids were collected with filtration, washed with water, and dried under high vacuum to give the desired crude product (5.87 g) as loose brown to yellow solid. 1H NMR (200 MHz, CDCl3): δ (ppm)=8.14-8.0 (m, 1H), 7.3-7.1 (m, 3H), 4.38 (q, 2H, J=7.1 Hz), 3.69 (s, 3H), 2.77 (s, 3H), 1.45 (t, 3H, J=7.1 Hz).

Aufarbeitung

  1. customquenched with diluted HCl solution
  2. additiondiluted with ice/water to a volume of ˜200 mL
  3. temperaturethe mixture was cooled with ice/water bath
  4. filtrationthe solids were collected with filtration
  5. washwashed with water
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c9c99943f4c4439aa5727f027386de43
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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