Water → 5-[6-(3-methoxy-prop-1-ynyl)-pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (37, 0.998 g, 4.09 mmol), 5-bromo-2-(3-methoxy-prop-1-ynyl)-pyridine (42, 0.616 g, 2.72 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.157 g, 0.136 mmol) were mixed in 8.2 mL of 1.00 M potassium carbonate in water (8.2 mmol) and 22 mL of tetrahydrofuran. The resulting mixture was heated at 80° C. Ethyl acetate and water were added, and the two layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and the filtrate concentrated under vacuum. The crude material was purified by silica gel flash chromatography. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (43, 565 mg). MS (ESI) [M+H+]+=264.3.

Provenance & Evidence