2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 50939593, compound

Participants

Reaction Steps

Prepared according to procedure Y by stirring (E)-4-chloro-5,7-difluoro-3-methyl-2-styrylquinoline (50 mg, 0.158 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo-[3,2-b]pyridin-6-yl)morpholine (37 mg, 0.158 mmol), Pd2dba3 (14.5 mg, 0.016 mmol), XPhos (15.1 mg, 0.032 mmol), sodium tert-butoxide (45.7 mg, 0.475 mmol), and toluene (1.6 mL) at 100° C. for 30 min. Purification by reverse-phase HPLC (0-70% acetonitrile in water) afforded 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-2-((E)-2-phenylethenyl)quinoline as a yellow solid. 1H NMR (500 MHz, chloroform-d) δ ppm 8.08 (1H, d, J=15.4 Hz), 7.69 (2H, d, J=7.3 Hz), 7.61-7.66 (1H, m), 7.55 (1H, d, J=2.2 Hz), 7.52 (1H, d, J=15.4 Hz), 7.41-7.47 (2H, m), 7.39 (1H, m), 6.92 (1H, t, J=2.8 Hz), 5.67 (1H, d, J=2.2 Hz), 3.79-3.88 (1H, m), 3.70-3.79 (4H, m), 3.64 (1H, d, J=9.0 Hz), 2.95-3.07 (4H, m), 2.45 (3H, s), 1.55 (3H, s), 1.52 (3H, s). Mass Spectrum (ESI) m/e=513.2 (M+1).

Provenance & Evidence