A mixture of 4-chloro-5-fluoro-3,8-dimethyl-2-(pyridin-2-yl)quinoline (30 mg, 0.11 mmol) (described herein), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]-pyridin-6-yl)morpholine (29.3 mg, 0.13 mmol) (described herein), Pd2dba3 (9.58 mg, 10.5 μmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (9.98 mg, 0.021 mmol), sodium tert-butoxide (30.2 mg, 0.314 mmol), and toluene (1.0 mL) was stirred at 100° C. for 18 h, then cooled to rt and concentrated. The resulting residue was taken up in EtOAc, washed with saturated aqueous sodium bicarbonate solution, 1M NaOH, and brine, and the organic layer dried (MgSO4) and concentrated. Chromatography afforded 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5-fluoro-3,8-dimethyl-2-(2-pyridin-yl)quinoline as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.69-8.76 (1H, m), 8.02-8.07 (1H, m), 7.92 (1H, td, J=7.7, 1.9 Hz), 7.50-7.56 (1H, m), 7.43-7.50 (1H, m), 7.34-7.43 (1H, m), 7.05 (1H, dd, J=12.2, 7.9 Hz), 5.70-5.75 (1H, m), 3.86 (1H, dt, J=8.9, 0.7 Hz), 3.68-3.79 (5H, m), 2.93-3.05 (4H, m), 2.79 (3H, s), 2.50 (3H, s), 1.56 (3H, s), 1.50 (3H, s). Mass Spectrum (ESI) m/e=484 (M+1).
