Reaction SMILES: C(P(C(C)(C)C)C1C(C)=C(C)C(C)=C(C)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:42]1[CH:57]=[CH:56][C:45]2[C@H:46]3[CH2:54][N:53]([CH3:55])[CH2:52][C@@H:47]3[CH2:48][NH:49][C:50](=[O:51])[C:44]=2[CH:43]=1.[CH2:58]([OH:65])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.[OH-].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC(C)(C)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:58]([O:65][C:42]1[CH:57]=[CH:56][C:45]2[C@H:46]3[CH2:54][N:53]([CH3:55])[CH2:52][C@@H:47]3[CH2:48][NH:49][C:50](=[O:51])[C:44]=2[CH:43]=1)[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1
Reactant: OCc1ccccc1
Reactant: CN1C[C@@H]2CNC(=O)c3cc(Cl)ccc3[C@H]2C1
Agent: [Pd+2]
Agent: CC(=O)[O-]
Agent: Cc1c(C)c(C)c(P(C(C)(C)C)C(C)(C)C)c(-c2c(C(C)C)cc(C(C)C)cc2C(C)C)c1C
Solvent: CCOC(C)=O
Solvent: COC(C)(C)C
Solvent: Cc1ccccc1
Product: CN1C[C@@H]2CNC(=O)c3cc(OCc4ccccc4)ccc3[C@H]2C1
Temperature: 95 °C
Reaction time: 1 h
Yield: 46.5 %

Procedure:
Palladium(II) acetate (1.075 g, 4.79 mmol), 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (2.76 g, 5.74 mmol), cesium carbonate (58.5, 179 mmol) and (3aS,10bS)-8-chloro-2-methyl-1,2,3,3a,4,5-hexahydrobenzo[e]pyrrolo[3,4-c]azepin-6(10bH)-one (Example 199, 30.0 g, 120 mmol) were charged to a three-neck 2-L round bottom flask equipped with a magnetic stir bar, thermocouple and a reflux condenser. The flask was purged with argon for about 2 hours. Toluene (240 mL) and benzyl alcohol (248 mL, 2393 mmol) were combined in a separate 1-L round bottom flask that was purged with argon for approximately 60 minutes. This mixture was transferred via cannula to the substrate-containing flask, under argon. The temperature was raised to 95° C. and the reaction solution was stirred at this temperature for 1 hour. The reaction mixture was cooled to room temperature and filtered. The reaction flask and funnel were rinsed with ethyl acetate. The solution was diluted with ethyl acetate (1 L) and then was washed with H2O (210 mL). The organic layer was then washed with a saturated aqueous solution of NaCl (220 mL). The combined aqueous layers were basified with an aqueous solution of 2 M KOH to neutral pH (7) and then seeded (Seed crystals were obtained by the process described for Example 199.) with about 20 mg of product. The solution was then further basified with 2 M KOH to pH=12. The solution was vigorously stirred for 30 minutes and then filtered. The solids were dried under an air flow for 1.5 hours. The solids were then dried under vacuum at room temperature. The material was dissolved in warm methanol and the solution was filtered. The filtrate was concentrated under reduced pressure to give a solid. To the solid was added a mixture of ethyl acetate and tert-butyl methyl ether (100 mL each). After stirring vigorously for 30 minutes, the product was collected by filtration and washed with tert-butyl methyl ether (200 mL) that had been pre-cooled to 0° C. The solids were placed in a vacuum oven, at room temperature, under a nitrogen flow for overnight drying. The solid was harvested to provide the title compound (18.0 g). An alternative preparation of the title compound is described in Example 274. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (dd, J=8.9, 5.3, 1H), 7.46-7.28 (m, 6H), 7.08-7.02 (m, 2H), 5.10 (s, 2H), 3.25-3.00 (m, 4H), 2.83 (dd, J=10.3, 8.6, 1H), 2.64-2.55 (m, 2H), 2.35 (s, 3H), 2.18-2.05 (m, 1H).