4-Chloro-5,7-difluoro-3-methyl-2-(1-methyl-1H-indol-5-yl)quinoline (44.1 mg, 0.129 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholine (30 mg, 0.129 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (12.3 mg, 0.026 mmol), Pd2dba3 (11.8 mg, 0.013 mmol), sodium tert-butoxide (37.1 mg, 0.386 mmol), and toluene (1.29 mL) were stirred at 105° C. for 2 h. The reaction mixture was then concentrated and the resulting residue partitioned between EtOAc and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine and water, then dried (MgSO4) and concentrated. Purification of the crude product by reverse-phase HPLC (0-70% 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-3-methyl-2-(1-methyl-1H-indol-5-yl)-quinoline. 1H NMR (400 MHz, chloroform-d) δ ppm 7.90 (1H, dd, J=1.6, 0.8 Hz), 7.69 (1H, ddd, J=9.6, 2.5, 1.4 Hz), 7.56 (1H, d, J=2.3 Hz), 7.43-7.53 (2H, m), 7.15 (1H, d, J=2.9 Hz), 6.95 (1H, ddd, J=11.8, 8.9, 2.6 Hz), 6.59 (1H, dd, J=3.1, 0.6 Hz), 5.77 (1H, d, J=2.3 Hz), 3.88 (3H, s), 3.84-3.86 (1H, m), 3.77 (4H, dd, J=5.1, 4.5 Hz), 3.72 (1H, d, J=9.4 Hz), 2.94-3.10 (4H, m), 2.36 (3H, s), 1.56 (3H, s), 1.50 (3H, s). Mass Spectrum (ESI) m/e=540.2 (M+1).
