1H-Pyrrolo(2,3-b)pyridine → 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

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 water (500 mL) and the mixture was extracted with CH2Cl2 (5×300 mL). The combined organic layers were washed with saturated brine, dried over MgSO4, filtered, concentrated and dried under high vacuum to give the title compound. MS: m/z=249 (M+1).

Provenance & Evidence