2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631460, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.018 g, 0.037 mmol), 2,5-dimorpholinopyridin-3-amine (0.074 g, 0.28 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)quinoline (0.084 g, 0.23 mmol) and Pd2dba3 (0.009 g, 0.009 mmol) and sodium tert-butoxide (0.056 g, 0.58 mmol) in toluene (2.3 mL) at 100° C. for 2.5 h. The crude product was purified by column chromatography on alumina (0-60% EtOAc/hexanes) to give the desired product N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(6-(pyrrolidin-1-yl)-pyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (1H, dd, J=2.4, 0.5 Hz), 7.84 (1H, dd, J=8.7, 2.4 Hz), 7.73 (1H, d, J=5.7 Hz), 7.56-7.62 (1H, m), 7.55 (1H, d, J=2.5 Hz), 7.39 (1H, ddd, J=13.2, 9.4, 2.4 Hz), 6.58 (1H, d, J=8.6 Hz), 6.39 (1H, d, J=2.7 Hz), 3.61-3.82 (8H, m), 3.47 (4H, t, J=6.6 Hz), 3.15 (2H, br. s.), 2.94-3.05 (4H, m), 2.84 (2H, br. s.), 2.13 (3H, s), 1.95-2.03 (4H, m). Mass Spectrum (ESI) m/e=588.2 (M+1).

Provenance & Evidence