2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 50906985, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (8.73 mg, 0.018 mmol), 2,5-dimorpholinopyridin-3-amine (0.036 g, 0.14 mmol), 1-(5-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2-yl)pyrrolidin-3-ol (0.043 g, 0.11 mmol), Pd2dba3 (0.004 g, 0.005 mmol) and sodium tert-butoxide (0.027 g, 0.29 mmol) in toluene (1.1 mL) at 100° C. for 2.5 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 1-(5-(4-(2,5-dimorpholinopyridin-3-ylamino)-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2-yl)pyrrolidin-3-ol. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (1H, d, J=2.2 Hz), 7.85 (1H, dd, J=8.8, 2.5 Hz), 7.74 (1H, d, J=6.1 Hz), 7.60 (1H, m), 7.56 (1H, d, J=2.5 Hz), 7.40 (1H, m), 6.58 (1H, d, J=9.2 Hz), 6.40 (1H, d, J=2.5 Hz), 5.00 (1H, m), 4.43 (1H, br. s.), 3.64-3.78 (8H, m), 3.55 (4H, m), 3.42 (4H, m), 3.00 (4H, d, J=4.9 Hz), 2.14 (3H, s), 1.95 (2H, br. s.). Mass Spectrum (ESI) m/e=604.3 (M+1).

Provenance & Evidence