1,2-Dimethoxyethane → 6-Chloro-1-(4-fluoro-2-methylphenyl)phthalazine

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A mixture of 1,6-dichlorophthalazine (5.39 g, 27.1 mmol), 4-fluoro-2-methylphenylboronic acid (5.00 g, 32.5 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.950 g, 1.35 mmol), and sodium carbonate (8.61 g, 81.2 mmol) in a 2:1 mixture of DME and EtOH (40 mL) was heated at 80° C. in an oil bath for 18 h. The mixture was cooled to room temperature, diluted with MeOH and filtered through a pad of Celite. The filtrate was concentrated over silica gel and purified using column chromatography (0-25% EtOAc in hexanes) to provide the title compound as a yellow crystalline solid. MS (ESI, pos. ion) m/z: 272.8 (M+1).

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