Potassium Carbonate → [2,6-dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)phenyl](1H-pyrrolo[2,3-c]pyridin-3-yl)methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of (4-bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (50 mg, 0.135 mmol), [1-(tert-butoxycarbonyl)-3,5-dimethyl-1H-pyrazol-4-yl]boronic acid (52 mg, 0.162 mmol), potassium carbonate (55 mg, 0.4 mmol), water (0.5 mL) and 1,1′bis(diphenylphosphino)ferrocene]dichloropalladium (II) (11 mg, 0.0135 mmol) in 1,4 dioxane (2 mL) was heated at 100° C. for 2 hours in a sealed vial. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting crude mass was purified by preparative thin layer chromatography using methanol in dichloromethane (10%) to afford [2,6-dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)phenyl](1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (0.012 g, 23%).

Provenance & Evidence