Toluene → 5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)-N-(2-(methylsulfonyl)-5-morpholinophenyl)quinolin-4-amine

Participants

Reaction Conditions

Reaction Steps

A screw-cap vial was charged with 4-chloro-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinoline (50 mg, 0.16 mmol), 2-(methylsulfonyl)-5-morpholinoaniline (Matrix Scientific; 50.5 mg, 0.20 mmol), XPhos precatalyst (CAS 1028206-56-5; 24.24 mg, 0.033 mmol), sodium tert-butoxide (39.4 mg, 0.41 mmol), and toluene (1.5 mL). The mixture was stirred at 95° C. under nitrogen gas for 3 h. The reaction was then cond and the resulting residue was dissolved in DCM. This solution was washed with water, dried over magnesium sulfate, and cond. The resulting crude product was purified by flash-chromatography (silica gel, 0-85% EtOAc in hexanes), affording 5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)-N-(2-(methylsulfonyl)-5-morpholinophenyl)quinolin-4-amine as a white solid. Mass Spectrum (ESI) m/e=525.3 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.62 (1H, d, J=6.5 Hz), 8.55 (1H, d, J=5.1 Hz), 7.79 (1H, d, J=9.0 Hz), 7.67-7.70 (1H, m), 7.62-7.67 (1H, m), 7.18-7.25 (1H, m), 6.96-7.04 (1H, m), 6.47-6.52 (1H, m), 5.98-6.01 (1H, m), 3.70-3.80 (4H, m), 3.17 (3H, s), 3.06-3.16 (4H, m), 2.49 (3H, s), 2.28 (3H, s).

Provenance & Evidence