Tetrahydrofuran → 3-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

Into a round bottom flask was added 3-Bromo-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (6, 2.8 g, 9.4 mmol) and tetrahydrofuran (100 mL). Tetrakis(triphenylphosphine)palladium(0) (500 mg, 0.50 mmol), 3,4-dimethoxyphenylboronic acid (2.1 g, 11 mmol) and 1 M K2CO3 solution (50 mL) The reaction mixture was stirred at 65° C. overnight. The reaction mixture was poured into water and extracted into ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The crude material was purified by column chromatography (gradient system of hexanes and ethyl acetate) to yield the titled compound, 1, (500 mg, 2 mmol, 20%) and 3-(3,4-dimethoxy-phenyl)-pyrrolo[2,4-b]pyridine-1-carboxylic acid tert-butyl ester (2.1 g, 5.9 mmol, 63%). The later compound can be easily converted to the desired compound, 1 by treatment with acid reagents such as TFA or HCl.

Provenance & Evidence