Acetonitrile → HCID 86698810, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-6-chloro-1H-indazole-3-carboxylic acid (100 mg, 0.36 mmol), 3-hydroxyphenylboronic acid (51.0 mg, 0.36 mmol), potassium carbonate (301 mg, 2.18 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (30.0 mg, 0.036 mmol) in toluene (1.5 mL) and water (1.1 mL) was degassed with N2 for 3 minutes and heated to 110° C. for 16 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The brown residue was acidified to pH 4 with 1N HCl and extracted with n-butanol (3×20 mL). The combined organic layers were washed with brine (2×20 mL), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by reverse phase HPLC (Column: Phenomenex Synergi C18 150×30 mm, 4 μm; 25% MeCN in water (0.225% TFA) to 45% MeCN in water (0.225% TFA) to afford the title compound (4 mg, 4% yield) as a white solid.

Provenance & Evidence