3-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline → (R)-2-(8-(3-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol

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3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (67.0 mg, 0.33 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (100 mg, 0.33 mmol), Palladium acetate (7.37 mg, 0.03 mmol), 2-(Dicyclohexylphosphino)biphenyl (11.50 mg, 0.03 mmol) and Cesium carbonate (321 mg, 0.98 mmol) were added to a microwave vial. 1,2-dimethoxyethane (2 mL) was added. The reaction mixture was flushed with argon and the mixture was run in a microwave for 60 minutes at 100°C. No product was observed. Additional catalyst and ligand were added and the reaction was run 1h @ 100°C. Still no reaction occurred. EtOH (0.500 mL) was added and another h @ 100°C was executed. Full conversion into product was observed. The solids were filtered off and the solvent was concentrated. The crude product was purified twice on Si. 20-80% MeOH in DCM. Yield: (R)-2-(8-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (33.0 mg, 21.28 %).

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