Reaction Steps
Prepared according to procedure N using 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-isopropyl-2-(pyridin-2-yl)quinoline (30 mg, 0.061 mmol), sodium tert-butoxide (11.73 mg, 0.122 mmol), morpholine (5.85 μL, 0.067 mmol), XPhos (5.82 mg, 0.012 mmol) and Pd2(dba)3 (5.6 mg, 6.11 μmol) in toluene (2.0 mL) and heating at 120° C. in the microwave for 90 min. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-(1-methylethyl)-2-(2-pyridinyl)quinoline was obtained as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, dd, J=4.9, 2.2 Hz), 7.86-7.93 (1H, m), 7.82 (1H, dd, J=9.8, 2.7 Hz), 7.66 (1H, d, J=7.4 Hz), 7.62 (1H, d, J=2.3 Hz), 7.53 (1H, dd, J=9.4, 5.9 Hz), 7.42 (1H, dd, J=7.4, 3.9 Hz), 7.17-7.25 (1H, m), 5.75 (1H, d, J=2.3 Hz), 3.80-3.93 (2H, m), 3.70-3.78 (4H, m), 3.34-3.48 (1H, m), 2.88-3.04 (4H, m), 1.62 (3H, s), 1.51 (3H, s), 1.29 (3H, d, J=7.0 Hz), 1.23 (3H, d, J=7.0 Hz). Mass Spectrum (ESI) m/e=498 (M+1).
