Reaktion #49877

Reaktionsgleichung

5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide

sodium hydride

chloromethyl methyl ether

→

5-methoxy-1-methoxymethyl-3-(1-methylethoxy)-1H-indole-2-carboxamide

Ausbeute 31.8%

Lösungsmittel

ethyl acetate

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with brine
2. 2
   TrocknenThe organic layer is dried over MgSO4
3. 3
   FiltrationFiltration
4. 4
   Einengenfollowed by concentration in vacuo and subsequent chromatography
5. 5
   Wascheneluting with 1:1 ethyl acetate

Vorschrift

5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide (106 mg, 0.43 mmol) in 4 mL of dimethylformamide is added to a suspension of sodium hydride (60% by weight) (30 mg, 0.75 mol) in 2 mL of dimethylformamide. After 1 hour chloromethyl methyl ether (60 μL, 0.79 mmol) is added, and the solution is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate and washed with brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and subsequent chromatography eluting with 1:1 ethyl acetate:hexane gives 40 mg of 5-methoxy-1-methoxymethyl-3-(1-methylethoxy)-1H-indole-2-carboxamide. An analytical sample was obtained by recrystallization from ethyl acetate:hexane; mp 145°-147° C.

Quelle