Reaction SMILES: CCN(CC)CC.[Si:8]([O:15]S(C(F)(F)F)(=O)=O)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[CH3:23][C:24]1[C:25]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[N:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][C:28]=2[C:34](=O)[CH3:35]>C(Cl)Cl>[Si:8]([O:15][C:34]([C:28]1[CH:29]=[CH:30][CH:31]=[C:32]2[C:27]=1[N:26]=[C:25]([NH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:24]([CH3:23])=[CH:33]2)=[CH2:35])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]
Reactant: CC(=O)c1cccc2cc(C)c(Nc3ccccc3)nc12
Reactant: CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F
Solvent: CCN(CC)CC
Solvent: ClCCl
Product: C=C(O[Si](C)(C)C(C)(C)C)c1cccc2cc(C)c(Nc3ccccc3)nc12
Temperature: 0 °C
Reaction time: 0.5 h

Procedure:
Et3N (0.241 mL, 1.728 mmol) and TBSOTf (0.318 mL, 1.383 mmol, added dropwise, over 2 min) were sequentially added to a solution of 1-(3-methyl-2-(phenylamino)quinolin-8-yl)ethanone (Example 105c; 308.1 mg, 0.691 mmol) in DCM (3.5 mL) at 0° C., and the resulting solution was stirred at 0° C. for 30 min. The mixture was then partitioned between DCM (50 mL) and saturated aq. NaHCO3 (20 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 to provide crude 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methyl-N-phenylquinolin-2-amine (450.0 mg) as a yellow-orange solid. This material was taken up in THF (3.50 mL), water (0.199 mL, 11.06 mmol) and NBS (123 mg, 0.691 mmol) were sequentially added at 0° C., and the resulting solution was stirred at 0° C. for 2 min. The mixture was partitioned between Et2O (50 mL) and water (30 mL). The organic layer was separated, sequentially washed with saturated aq. NaHCO3 (20 mL), water (20 mL), and brine (20 mL), and then dried over Na2SO4, filtered, and concentrated in vacuo to provide crude 2-bromo-1-(3-methyl-2-(phenylamino)quinolin-8-yl)ethanone (404.1 mg) as a yellow-orange solid. NH4OAc (213 mg, 2.77 mmol) and 4-ethoxy-5-ethyl-5,6-dihydropyridin-2(1H)-one (prepared according to Synthesis 2007, 3185-3190; 140 mg, 0.830 mmol) were added to the resulting solid. The mixture was taken up in EtOH (3.5 mL) and heated in a sealed flask under argon at 50° C. for 16 h. The mixture was then cooled to 25° C. and concentrated in vacuo. The residue was partitioned between DCM (50 mL) and sat. aq. NaHCO3 (30 mL). The aq. layer was extracted with DCM (3×30 mL), and the combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished rac-7-ethyl-2-(3-methyl-2-(phenylamino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (80.6 mg, 0.203 mmol, 29% yield) as a yellow solid: 1H NMR (400 MHz, CD Cl3) δ ppm 12.34 (1H, br. s.), 7.96 (1H, dd, J=7.5, 1.1 Hz), 7.83 (1H, s), 7.52 (2H, d, J=7.6 Hz), 7.45 (1H, dd, J=7.8, 1.0 Hz), 7.41 (2H, t, J=7.8 Hz), 7.30 (1H, t, J=7.7 Hz), 7.21 (1H, t, J=7.5 Hz), 7.10 (1H, d, J=2.2 Hz), 6.44 (1H, br. s.), 5.22 (1H, br. s.), 3.63 (1H, ddd, J=12.0, 5.5, 2.1 Hz), 3.23 (1H, ddd, J=12.0, 6.2, 3.1 Hz), 2.46-2.54 (1H, m), 2.45 (3H, s), 1.14-1.23 (1H, m), 1.02-1.12 (1H, m), 0.65 (3H, t, J=7.4 Hz). m/z (ESI, +ve) 397.2 (M+H)+. Separation of this material by supercritical-fluid chromatography (Chiralcel AD-H (250×21 mm, 5 μm), 55% liquid CO2/45% MeOH (+20 mM NH3), 60 mL/min) separately afforded 7-ethyl-2-(3-methyl-2-(phenylamino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one, first-eluting enantiomer (117; 27.0 mg, 0.068 mmol) and 7-ethyl-2-(3-methyl-2-(phenylamino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one, second eluting enantiomer (118; 27.8 mg, 0.070 mmol).