[(3-Bromophenyl)methyl]methylamine (0.059 ml, 0.432 mmol), 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 52) (150 mg, 0.360 mmol), and potassium carbonate (74.7 mg, 0.540 mmol) were mixed together in ethanol (1.2 mL) and toluene (1.2 mL) and the reaction mixture was degassed using house vacuum and quenched several times with nitrogen tetrakis(triphenylphosphine)palladium(0) (20.82 mg, 0.018 mmol) was added and the reaction was degassed again and then stirred under nitrogen at 90° C. for 16 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between EtOAc (15 mL) and water (5 mL) and the layers were separated. The organic layer was washed with brine (5 mL), dried using phase separator and concentrated in vacuo to give a first residue. The aqueous phase was washed with further EtOAc (20 mL) and the organic phase was dried using a phase separator then concentrated in vacuo to give a second residue which was mixed with the first one. Purification of the combined residues by flash chromatography on silica gel (gradient: 5 to 25% (2M NH3 in MeOH) in DCM) gave a residue which was further purified by flash chromatography on silica gel (gradient: 5 to 25% (2M NH3 in MeOH) in AcOEt) to give a second residue. This residue was dissolved in DCM (3 mL) and HCl (1.25 M in MeOH, 0.129 ml, 0.161 mmol) was added. The resulting mixture was concentrated in vacuo to give 1-methylethyl((2S,4R)-1-acetyl-2-methyl-6-{3-[(methylamino)methyl]phenyl}-1,2,3,4-tetrahydro-4-quinolinyl)carbamate hydrochloride (50 mg, 0.107 mmol, 29.6% yield) as a white solid.
