Ethanol → 1H-Pyrrolo[2,3-c]pyridine-4-carboxylic acid, 1-(4-fluorophenyl)-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-1-(4-fluorophenyl)-1H-pyrrolo[2,3-c]pyridine (820.0 mg, 2.82 mmol), Et3N (1.00 mL, 7.19 mmol), Pd[PhCN]2Cl2 (45 mg, 0.12 mmol), and dppf (155 mg, 0.28 mmol) in absolute ethanol (20 mL) is placed in a pressure reactor with stirring and placed under 15 bars of carbon monoxide and warmed at 140° C. After 2 hours, the pressure reactor is cooled to room temperature, returned to atmopheric pressure and opened. The reaction is diluted with ammonium chloride and extracted with EtOAc (3×25 mL). The combined organic layers are washed with brine (2×10 mL), dried over magnesium sulfate, filtered and concentrated. The crude material is purified by silica gel chromatography using a gradient of 5-25% EtOAc in hexanes to afford 1-(4-fluorophenyl)-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid ethyl ester.

Provenance & Evidence