2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 67507706, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.022 g, 0.047 mmol), 2,5-dimorpholinopyridin-3-amine (0.093 g, 0.351 mmol), 1-(5-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2-yl)-N,N-dimethylpyrrolidin-3-amine (0.118 g, 0.29 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.070 g, 0.73 mmol) in toluene (2.9 mL) at 100° C. for 2 h. The crude product was purified by column chromatography on silica gel (0 to 100% DCM/methanol/ammonium hydroxide (90/9/1)) to give the desired product 2-(6-(3-(dimethylamino)pyrrolidin-1-yl)pyridin-3-yl)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methylquinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (1H, d, J=2.0 Hz), 7.85 (1H, dd, J=8.7, 2.4 Hz), 7.74 (1H, d, J=5.9 Hz), 7.59 (1H, m), 7.55 (1H, d, J=2.5 Hz), 7.39 (1H, ddd, J=13.3, 9.3, 2.4 Hz), 6.61 (1H, d, J=8.6 Hz), 6.40 (1H, d, J=2.5 Hz), 3.58-3.82 (10H, m), 3.39 (1H, m), 3.21-3.10 (3H, br. m), 2.95-3.04 (4H, m), 2.90-2.75 (3H, br. m), 2.22 (6H, s), 2.18 (1H, m), 2.13 (3H, s), 1.83 (1H, m). Mass Spectrum (ESI) m/e=631.2 (M+1).

Provenance & Evidence