Potassium Carbonate → 3-[1-(4-Chloro-benzyl)-5-(pyridin-2-ylmethoxy)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

3-[1-(4-Chlorobenzyl)-5-hydroxy-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester (0.100 g, 0.26 mmol) was dissolved in acetone (2 mL), and 2-chloromethyl-pyridine (0.064 g, 0.39 mmol), tetrabutylammonium iodide (0.095 g, 0.26 mmol) and K2CO3 (0.107 g, 0.77 mol) were added. The mixture was stirred at 65° C. overnight, and two products were observed by TLC analysis. The reaction was cooled to room temperature, diluted with water, and extracted with EtOAc three times. The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated to give a 1:2 mixture of the O-alkylated and N-alkylated products. The crude material was purified by preparative TLC to obtain the O-alkylated title compound.

Provenance & Evidence