Toluene → HCID 59631369, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.018 g, 0.038 mmol), 2,5-dimorpholinopyridin-3-amine (0.074 g, 0.281 mmol), 4,6-dichloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.072 g, 0.234 mmol) and Pd2dba3 (8.59 mg, 9.38 μmol) in toluene (2.3 mL, 0.23 mmol) was added sodium t-butoxide (0.056 g, 0.59 mmol). The reaction mixture was heated to 120° C. and stirred for 45 min. The reaction was cooled to rt and diluted with water (25 mL). The mixture was extracted with EtOAc (2×10 mL) and DCM (1×10 mL). The organic layers were combined and dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (0 to 100% EtOAc/DCM) to give the desired product 6-chloro-N-(2,5-di-4-morpholinyl-3-pyridinyl)-5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.70 (1H, dd, J=4.7, 1.2 Hz), 7.90 (3H, m), 7.57-7.73 (3H, m), 7.39 (1H, m), 6.41 (1H, s), 3.94 (4H, br. s.), 3.80 (4H, br m), 3.22 (4H, br. s.), 3.06 (4H, br m), 2.26 (3H, s). Mass Spectrum (ESI) m/e=535.3 (M+1).

Provenance & Evidence