Benzyl Bromide → HCID 59490887, compound

Participants

Reaction Steps

3-(2-Fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester A5 (0.02 g, 0.07 mmol) was diluted with DMF (1 mL). To the resulting solution was added benzyl bromide (0.1 mmol) and sodium hydride (0.077 mmol). The resulting suspension was stirred at room temperature for 14 hours, then ethyl acetate (50 mL) and water (20 mL) were added to the reaction mixture and layers were separated. The organic layer was sequentially washed with aqueous saturated sodium bicarbonate solution (10 mL), water (10 mL) and saturated brine (10 mL). The separated organic solution was dried (magnesium sulfate), filtered and concentrated in vacuo to provide a crude residue which was purified using flash chromatography to provide 1-Benzyl-3-(2-fluoro-phenyl)-5-methyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester A6 (94% yield). MS: 389.2 (M+H)+.

Provenance & Evidence