Reaction SMILES: C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CN(C1CCCCC1)C1CCCCC1.Br[C:29]1[CH:30]=[CH:31][C:32](=[O:50])[N:33]([CH2:35][CH2:36][O:37][C:38]2[C:47]3[C:42](=[CH:43][C:44]([O:48][CH3:49])=[CH:45][CH:46]=3)[N:41]=[CH:40][CH:39]=2)[CH:34]=1.[CH2:51]1[CH2:56][O:55][CH:54]=[CH:53][CH2:52]1>C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[O:55]1[CH2:56][CH2:51][CH:52]=[CH:53][CH:54]1[C:31]1[C:32](=[O:50])[N:33]([CH2:35][CH2:36][O:37][C:38]2[C:47]3[C:42](=[CH:43][C:44]([O:48][CH3:49])=[CH:45][CH:46]=3)[N:41]=[CH:40][CH:39]=2)[CH:34]=[CH:29][CH:30]=1
Reactant: C1=COCCC1
Reactant: COc1ccc2c(OCCn3cc(Br)ccc3=O)ccnc2c1
Agent: [Pd]
Agent: CC(C)(C)P(C(C)(C)C)C(C)(C)C
Agent: CN(C1CCCCC1)C1CCCCC1
Solvent: C1COCCO1
Solvent: ClCCl
Product: COc1ccc2c(OCCn3cccc(C4C=CCCO4)c3=O)ccnc2c1
Temperature: 100 °C
Reaction time: 0.25 h

Procedure:
A 10 mL Schlenk-type flask was charged with tris(dibenzylideneacetone)dipalladium (0) (0.036 g, 0.039 mmol), 2 mL dioxane, and swept with Ar. To the solution was added tri-tert-butylphosphine (0.16 g, 0.079 mmol), N-methyldicyclohexylamine (0.077 g, 0.39 mmol) and a stirrer bar. The solution was stirred for 15 min, and treated with 5-bromo-1-(2-(7-methoxyquinolin-4-yloxy)ethyl)pyridin-2(1H)-one (0.0295 g, 0.079 mmol) followed by 2H-3,4-dihydropyran (0.14 mL, 1.6 mmol). The solution was heated to 100° C. for 72 h, and cooled. To the solution was added Silica carbonate (Silicycle, Inc., 0.23 g, 0.16 mmol). The slurry was stirred for 15 min, diluted with 2 mL CH2Cl2 and filtered. The silica was washed with 20 mL CH2Cl2, and the filtrate was concentrated in vacuo. The residue was dissolved in 2 mL THF and treated with Silica Propyl sulfonic acid (Silicycle, Inc., 0.37 g, 0.27 mmol). The slurry was stirred for 20 min, and filtered. The Silica was washed with THF (5 mL), and EtOH (5 mL). The filtrates were discarded. The silica was eluted with 2N NH3 in EtOH (5 mL), followed by 10 mL EtOH. The filtrate was concentrated in vacuo. The residue was loaded onto a 19×150 mm Waters Xterra Prep C18 OBD column (100 Å pore diameter, 5 μm particle size, spherical shape, PN 186002381; Gradient: 0→5 min@20 mL/min, 25% B; 5.0→35 min@20 mL/min, linear gradient to 55% B; 35→45@20 mL/min, isocratic at 55% B, 45→55 min@20 mL/min, step to 100% B; 55→60 min@20 mL/min, step to 25% B; 60 min end). A=10 mM NH4 Carbonate in water, pH 8.6, B=ACN. A band that eluted from 4.6-5.1 minutes was isolated. The solvent was removed in vacuo to afford 5-(5,6-dihydro-2H-pyran-2-yl-1-(2-(7-methoxyquinolin-4-yloxy)ethyl)pyridin-2(1H)-one. 1H NMR (400 MHz, CDCl3) δ ppm 1.97 (br. s., 1 H) 3.94 (s, 3H) 4.46 (td, J=5.18, 1.27 Hz, 2H) 4.53 (td, J=5.18, 1.27 Hz, 2H) 6.21 (td, J=6.70, 1.37 Hz, 1H) 6.60 (ddd, J=9.17, 1.25, 0.73 Hz, 1H) 6.64 (d, J=5.38 Hz, 1H) 7.14 (dd, J=9.10, 2.54 Hz, 1H) 7.35 (ddd, J=9.17, 6.77, 1.96 Hz, 1H) 7.37 (d, J=2.35 Hz, 1H) 7.96 (d, J=9.10 Hz, 1H) 8.65 (d, J=5.28 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ ppm 49.49 (s, 1 C) 55.48 (s, 1 C) 65.74 (s, 1 C) 99.46 (s, 1 C) 105.95 (s, 1 C) 107.20 (s, 1 C) 115.66 (s, 1 C) 118.61 (s, 1 C) 121.11 (s, 1 C) 122.56 (s, 1 C) 138.49 (s, 1 C) 140.07 (s, 1 C) 151.07 (s, 1 C) 151.63 (s, 1 C) 160.86 (s, 1 C) 161.04 (s, 1 C) 162.60 (s, 1 C). MS (ESI pos. ion) m/z (MH+): 297.1, calcd for C17H16F3N2O3+H+=297.1.