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: ClCCl
Solvent: CCN(CC)CC
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 (0.203 mL, 1.457 mmol) and TBSOTf (0.281 mL, 1.224 mmol, added dropwise, over 2 min) were sequentially added to a solution of 1-(3-methyl-2-(phenylamino)quinolin-8-yl)ethanone (161 mg, 0.583 mmol) in DCM (3.0 mL) at 0° C., and the resulting solution was stirred at 0° C. for 30 min. The resulting mixture was 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 then dried over Na2SO4, filtered, and concentrated in vacuo to provide 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methyl-N-phenylquinolin-2-amine as a yellow-orange oil. This material was taken up in THF (3.0 mL), water (0.168 mL, 9.32 mmol) and NBS (104 mg, 0.583 mmol) were sequentially added, and the resulting solution was stirred at 25° C. for 15 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 MgSO4, filtered, and concentrated in vacuo to provide 2-bromo-1-(3-methyl-2-(phenylamino)quinolin-8-yl)ethanone (250 mg) as a yellow-orange solid (containing ca. 30 wt % 2-bromo-1-(2-((4-bromophenyl)amino)-3-methylquinolin-8-yl)ethanone). NH4OAc (180 mg, 2.331 mmol) and piperidine-2,4-dione (79 mg, 0.699 mmol) were added to this solid, and the mixture was taken up in EtOH (3.0 mL) and stirred at 25° C. for 5 min. The reaction vial was then sealed under argon and heated at 50° C. for 14 h. The mixture was cooled to 25° C. and concentrated in vacuo. The residue was partitioned between DCM (50 mL) and saturated 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, 0-10% DCM/MeOH) followed by rpHPLC of the collected solid (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% ACN/H2O+0.1% TFA) separately provided 2-(3-methyl-2-(phenylamino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 2,2,2-trifluoroacetate (20.5 mg, 0.042 mmol, 7% yield) as a yellow solid (following trituration of initially obtained oil with Et2O): 1H NMR (400 MHz, MeOH-d4) δ ppm 8.30 (1H, br. s.), 7.79 (2H, d, J=7.4 Hz), 7.62 (2H, t, J=7.8 Hz), 7.50-7.57 (3H, m), 7.44 (1H, t, J=7.6 Hz), 6.57 (1H, s), 3.53 (2H, t, J=7.2 Hz), 2.78 (2H, t, J=6.8 Hz), 2.56 (3H, s). 19F NMR (377 MHz, MeOH-d4) δ ppm −77.49 (3F, s). m/z (ESI, +ve) 369.2 (M+H)+. 2-(2-((4-bromophenyl)amino)-3-methylquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 2,2,2-trifluoroacetate (6.9 mg, 0.012 mmol, 2% yield) as an orange oil: 1H NMR (400 MHz, MeOH-d4) δ ppm 8.14 (1H, br. s.), 7.85 (1H, d, J=7.5 Hz), 7.69 (3H, d, J=8.6 Hz), 7.44-7.50 (2H, m), 7.43 (1H, t, J=7.9 Hz), 6.77 (1H, s), 3.56 (2H, t, J=7.1 Hz), 2.70 (2H, t, J=7.0 Hz), 2.52 (3H, s). 19F NMR (377 MHz, MeOH-d4) δ ppm −77.51 (3F, br. s.). m/z (ESI, +ve) 447.0 (M+H)+.