Water → 6-phenyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromo-1-benzoyl-1H-pyrrolo[2,3-b]pyridine (0.19 g, 0.64 mmol) obtained in Example A47, Step 1 in 1,2-dimethoxyethane (5.0 mL) was successively added with water (2.0 mL), phenylboronic acid (0.16 g, 0.64 mmol), and sodium carbonate (0.20 g, 1.9 mmol). After the inside of the reaction vessel was replaced with argon, the reaction mixture was added with tetrakis(triphenylphosphine)palladium(0) (0.074 g, 0.064 mmol), and the mixture was stirred overnight at 110° C. in a sealed tube. The reaction mixture was extracted with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→99:5)) to obtain 6-phenyl-1H-pyrrolo[2,3-b]pyridine (0.10 g, 80%).

Provenance & Evidence