6-(((2S,4R)-1-Acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile (for a preparation see Intermediate 2)(3.25 g, 8.44 mmol), {6-[(methyloxy)carbonyl]-3-pyridinyl}boronic acid (1.832 g, 10.12 mmol), {6-[(methyloxy)carbonyl]-3-pyridinyl}boronic acid (1.832 g, 10.12 mmol) and triethylamine (2.352 ml, 16.87 mmol) were combined in MeOH (30 ml) and DME (5 ml). The reaction mixture was divided between 2 vials and each heated at 120° C. for 45 min. The crude reaction mixtures were combined and concentrated in vacuo to give 4.4 g of crude brown solid. This was purified by chromatography on silica (100 g), eluting with over 1500 ml of EtOAc (compound leached off slowly) to give methyl 5-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinate (2.94 g, 6.66 mmol, 79% yield) as a brown foamy solid. LCMS (Formate, 2 min), Rt=0.81 min, MH+=442.
