5-Fluoro-o-toluidine → 1-(4-fluoro-2-methylphenyl)-N-(5-fluoro-2-methylphenyl)phthalazin-6-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-1-(4-fluoro-2-methylphenyl)phthalazine (200 mg, 0.73 mmol), 5-fluoro-2-methylaniline (138 mg, 1.1 mmol), tris(dibenzylideneacetone)dipalladium (0) (34 mg, 0.037 μmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (35 mg, 0.073 mmol), and sodium tert-butoxide (211 mg, 2.2 mmol) in toluene (2 mL) was heated at 100° 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 (0-40% acetone in hexanes) to afford a tan solid that was about 90% pure. The material was dissolved in MeOH and loaded onto an Agilent AccuBOND II SCX solid phase extraction column. It was washed with MeOH followed by 2 M NH3 in MeOH. The title compound was obtained as a tan solid. MS (ESI, pos. ion) m/z: 362.1 (M+1).

Provenance & Evidence