Potassium Carbonate → 5-(4-Acetylphenyl)-6-chloro-1H-indazole-3-carboxylic acid

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Reaction Steps

To a mixture of 5-bromo-6-chloro-1H-indazole-3-carboxylic acid (200 mg, 0.73 mmol) and 4-acetylphenylboronic acid (131 mg, 0.80 mmol) in toluene (2 mL) and EtOH (1 mL) was added 2N aqueous potassium carbonate solution (1.45 mL, 2.90 mmol). The resulting mixture was degassed with N2 for 10 minutes, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (29 mg, 0.036 mmol), and heated to reflux for 16 hours. The cooled reaction was quenched with saturated NH4Cl and the mixture was filtered. The filtrate was acidified with 1N HCl to pH 5 and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting crude material was purified by reverse phase chromatography (Biotage C18 column, 0-40% MeCN/water) to give the title compound (82 mg, 40% yield) as a solid.

Provenance & Evidence