Dimethylformamide → 1-((2-(Trimethylsilyl)ethoxy)methyl)-1,3-dihydro-2H-pyrrolo(2,3-b)pyridin-2-one

Reaktionsgleichung

[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:4]1.[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17]Cl.CN(C=[O:25])C>>[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17][N:3]1[C:11]2=[N:10][CH:9]=[CH:8][CH:7]=[C:6]2[CH2:5][C:4]1=[O:25]

Komponenten

Edukt 4

HCID 6228Dimethylformamide

HCID 92221H-Pyrrolo(2,3-b)pyridine

HCID 24758Sodium hydride

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Produkt 1

HCID 574588861-((2-(Trimethylsilyl)ethoxy)methyl)-1,3-dihydro-2H-pyrrolo(2,3-b)pyridin-2-one

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil; 16.2 g, 0.404 mol) was added in portions over 25 min to a solution of 7-azaindole (39.8 g, 0.337 mol) in DMF (200 mL) at 0 □C and the mixture was stirred for 1 h. 2-(Trimethylsilyl)ethoxymethyl chloride (71.8 mL, 0.404 mol) was then added slowly over 15 min, keeping the temperature of the reaction mixture below 10 □C. After 1 h, the reaction was quenched with H2O (500 mL) and the mixture was extracted with CH2Cl2 (5×300 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, concentrated and dried under high vacuum to give the title compound. MS: m/z=249 (M+1).