[Br:1][C:2]1[C:3]([CH:12]=O)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:14]([NH2:16])[CH3:15].C(O)(=O)C.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[C:3]([CH2:12][NH:16][CH2:14][CH3:15])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=23-Bromo-quinoline-2-carbaldehyde (3.34 g, 16.3 mmol), ethylamine (2M in MeOH; 9.78 mL, 19.6 mmol), and acetic acid (1.02 mL, 17.8 mmol) were combined in MeOH (25 mL) and stirred at 0° C. for 30 minutes. Sodium cyanoborohydride (1.53 g, 24.5 mmol) was added, and the reaction was monitored by analytical LCMS. The mixture was worked-up with saturated aqueous NaHCO3 and extracted with CH2Cl2, and the residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give the title compound.
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