To a solution of 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (3.37 g, 11.0 mmol) in dioxane (50 mL) were added N-(Boc)-propargylamine (1.705 g, 11.0 mmol), Pd(PPh3)4 (0.250 g, 2 mol %), CuI (0.04 g), and NEt3 (1.85 mL, 13.2 mmol). The mixture was heated under nitrogen at 80° C. for 48 h. The reaction mixture was concentrated, taken up with CH2Cl2 (120 mL), washed with water (3×30 mL), dried over Na2SO4, filtered, and concentrated at reduced pressure. The crude material was purified by column chromatography on silica gel using EtOAc/Hexanes (1:4) to give the title compound. 1H NMR (CDCl3, 300 MHz): δ=1.56 (s, 9H), 4.22 (d, J=2.4 Hz, 2H), 4.99 (bs, 1H), 7.40-7.61 (m, 4H), 7.88 (d, J=6.8 Hz, 1H), 8.05-8.08 (m, 2H), 8.32 (d, J=1.8 Hz, 1H), MS (ES+): m/z=381.14 (100) [MH+]. HPLC: tR=3.87 min (ZQ3, polar—5 min).
