p-Toluidine → HCID 11473837, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,4-dichloro-6-(5-chloro-2-methoxy-phenyl)-pyridine (25 mg, 0.087 mmol), p-tolylamine (10.2 mg, 0.1 mmol), sodium tert-butoxide (26 mg, 0.26 mmol), and tetrahydrofuran (15 ml), degassed with argon, was added palladium acetate (15 mg, 0.066 mmol) followed by 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (30 mg, 0.048 mmol). The mixture was stirred at 70° C. for 5 hours and filtered through a pad of celite under suction. The filtrate was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography eluting with ethyl acetate-hexane (1:9) to provide the title compound (6.6 mg, 21% yield). 1H NMR (acetone-d6) δ 2.32 (s, 3H, CH3), 3.95 (s, 3H, CH3), 6.83–6.84 (m, 1H, Ar), 7.15 (d, 2H, J=8.2 Hz, Ar), 7.20 (d, 1H, J=8.9 Hz, Ar), 7.43 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.46 (d, 1H, J=1.5 Hz, Ar), 7.57–7.60 (m, 2H, Ar), 8.10 (d, 1H, J=2.7 Hz, Ar), 8.43 (s, 1H, NH).

Provenance & Evidence