A solution of 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 53.5 mg, 0.180 mmol), 2-chloroaniline (94 μl, 0.898 mmol), and LHMDS (1.0 M in THF; 898 μl, 0.898 mmol) was stirred in a sealed flask at 65° C. for 4 h. The mixture was then partitioned between DCM (50 mL) and saturated aq. NH4Cl (30 mL). The organic layer was separated, and the aq. layer was extracted with DCM (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by supercritical-fluid chromatography (Chiralcel OJ-H (250×21 mm, 5 μm), 55% liquid CO2/45% 1:1:1 MeOH:EtOH:IPA (+20 mM aq. NH4OH), 75 mL/min) separately provided 2-(2-((2-chlorophenyl)amino)-quinolin-8-yl)-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (107; 9.7 mg, 0.025 mmol, 14% yield; first-eluting compound) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.47 (1H, br. s.), 9.73 (1H, br. s.), 8.17 (2H, t, J=8.9 Hz), 8.06 (1H, d, J=9.0 Hz), 7.59 (2H, t, J=7.6 Hz), 7.39 (3H, quin, J=7.8 Hz), 7.22 (1H, t, J=7.6 Hz), 6.99 (2H, d, J=8.6 Hz), 6.94 (1H, s), 6.08 (1H, d, J=7.0 Hz). m/z (ESI, +ve) 387.0 (M+H)+: and 2-(2-((2-chlorophenyl)amino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (108; 14.0 mg, 0.036 mmol, 20% yield; second-eluting compound) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.16 (1H, s), 8.04 (3H, t, J=8.7 Hz), 7.53 (2H, d, J=8.0 Hz), 7.35-7.41 (1H, m), 7.31 (2H, t, J=7.8 Hz), 7.09-7.18 (2H, m), 6.95 (1H, d, J=8.8 Hz), 5.32 (1H, br. s.), 3.53-3.60 (2H, m), 2.68 (2H, br. s.). m/z (ESI, +ve) 389.1 (M+H)+.
