[NH2:1][C:2]1[C:9]([OH:10])=[C:8]([F:11])[C:7](Br)=[C:6](C)[C:3]=1[C:4]#[N:5].[Cl:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.[C:24](=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[NH2:1][C:2]1[C:3]([CH3:24])([C:4]#[N:5])[CH2:6][C:7]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:14])[CH:20]=2)=[C:8]([F:11])[C:9]=1[OH:10]2-Amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-75) (2.0 g, 8.16 mmol), 3-chlorophenylboronic acid (2.63 g, 16.3 mmol) and cesium carbonate (5.32 g, 16.3 mmol) were dissolved in 1,4-dioxane (90 ml)/water (10 ml), and at room temperature, (tetrakistriphenylphosphine)palladium(0) (943 mg, 0.82 mmol) was added. The solution was stirred in a nitrogen steam at 100° C. for 12 hours. After cooling to room temperature, the insoluble matter was separated by filtration with washing with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, this was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:ethyl acetate=95:5, v/v) to obtain the entitled compound (1.76 g, 78%) as a pale brown solid.
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