Water → HCID 59490907, compound

Participants

Reaction Conditions

Reaction Steps

3-Iodo-5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid methyl ester C3 (0.3 g, 0.9 mmol) was diluted with 1,2-dimethoxyethane (5 mL) and to the resulting solution was added PdClz2 (dppf)2 (0.074 g, 10 mol %). The reaction was heated to 90° C. and allowed to stir at this temperature for 30 minutes. Pyridyl boronic acid (0.415 g, 2.7 mmol), potassium carbonate (0.621 g, 5 mmol), and water (0.3 mL) were then added to the reaction mixture in three portions over 5 minutes. The resulting reaction allowed to stir at 90° C. for an additional minutes, then the reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and filtered through a celite plug. The filtrate was concentrated in vacuo and the resulting residue was purified using flash chromatography to provide 5-methoxy-3-(2-methoxy-pyridin-3-yl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid methyl ester C4 (0.075 g, 27% yield). MS: 314.2 (M+H)+.

Provenance & Evidence