Phenacyl bromide → HCID 19916779, compound

Participants

Reaction Steps

3-(Carbamoylmethyl)-2-phenylpyrrolo[2,3-b]pyridine (0.35 g, 1.4 mmol) and phenacyl bromide (0.33 g) in acetonitrile (5 ml) were refluxed under argon for 3 h. The resulting yellow suspension was isolated by filtration (0.4 g). The sparingly soluble raw product was dissolved in a mixture of methanol (20 ml) and methylene chloride (480 ml), loaded on a flash chromatography column (SiO2 /CH2Cl2 :MeOH 96:4), and eluted with a) 1000 ml MeOH:CH2Cl2 2.5:97.5; b) 1000 ml MeOH:CH2Cl2 5:95; c) 1000 ml MeOH:CH2Cl2 1:9 to afford pure 3-(carbamoylmethyl)-7-phenacyl-2-phenylpyrrolo[2,3-b]pyridine which was isolated as its hydrobromide (0.14 g, 22%).

Provenance & Evidence