Methyl iodide → Methyl 1-methyl-1H-indole-3-carboxylate

HRID 1297353

Reaktionsgleichung

Reaktionsgleichung von HRID 1297353
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1.[CH3:16]I>CN(C=O)C.O>[CH3:16][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 589098Methyl indole-3-carboxylate

Produkt 1

HCID 842006Methyl 1-methyl-1H-indole-3-carboxylateAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

NaH (60% dispersion in mineral oil, 8.56 g, 214.0 mmole) was added portionwise, allowing for gas evolution, to a solution of methyl 1H-indole-3-carboxylate (25.00 g, 142.7 mmole) in DMF (350 mL) at 0° C. When the NaH addition was complete, methyl iodide (44.4 mL, 713.5 mmole) was added at 0° C. The reaction was stirred at 0° C. for 15 minutes then at RT overnight. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were dried over K2CO3 and concentrated to afford the title compound (26.00 g, 96%) as an orange solid: MS (ES) m/e 190 (M+H)+.

Aufarbeitung

  1. customat RT
  2. customovernight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over K2CO3
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-57bb5209b7f64520afe125b22fee0872
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250424B2

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