Potassium Carbonate → HCID 68652930, compound

Participants

Reaction Steps

Compound 5a (0.75 mL of the nominally 1.0 M solution, 0.75 mmol) was added via syringe to 7-chloro-3-[2-methoxy-4-(pyrazol-1-yl)phenyl]-1,5-dimethyl pyrazolo[4,3-b]pyridine (compound 4b, 200 mg, 0.57 mmol) under nitrogen and the mixture was evaporated to dryness. Dioxane (2 mL) and water (2 mL) were added, followed by potassium carbonate (157 mg, 1.14 mmol) and tetrakis (triphenylphosphine)palladium(0) (66 mg, 0.057 mmol). The mixture was stirred and heated to reflux for 6 hr and then was allowed to cool. Water (5 mL) was added and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, concentrated, and the residue was chromatographed on silica gel using 1:2 hexanes/ethyl acetate to afford 7-(2-phenyl-1-ethenyl)-3-[2-methoxy-4-(pyrazol-1-yl)phenyl]-1,5-dimethylpyrazolo[4,3-b]pyridine (compound 5b, 201 mg) as a yellow oil.

Provenance & Evidence