2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-2-(3-methoxybenzyl)-3-methylquinoline

Participants

Reaction Steps

Prepared according to procedure Y by stirring 4-chloro-5,7-difluoro-2-(3-methoxybenzyl)-3-methylquinoline (50 mg, 0.150 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (35.0 mg, 0.150 mmol), Pd2dba3 (13.7 mg, 0.015 mmol), XPhos (14.3 mg, 0.030 mmol), sodium tert-butoxide (43 mg, 0.449 mmol), and toluene (1.5 mL) at 100° C. for 30 min. Purification by reverse-phase HPLC (0-90% acetonitrile in water) gave 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-2-(3-methoxybenzyl)-3-methylquinoline. 1H NMR (400 MHz, chloroform-d) δ ppm 7.59-7.66 (1H, m), 7.47-7.54 (1H, m), 7.15-7.23 (1H, m), 6.91-7.00 (1H, m), 6.72-6.83 (3H, m), 5.50-5.56 (1H, m), 4.34-4.44 (2H, m), 3.78-3.83 (1H, m), 3.67-3.74 (7H, m), 3.51-3.59 (1H, m), 2.92 (4H, q, J=5.1 Hz), 2.16-2.23 (3H, m), 1.47-1.54 (3H, m), 1.40-1.47 (3H, m). Mass Spectrum (ESI) m/e=531.2 (M+1).

Provenance & Evidence