To a solution of (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (497 mg, 1.00 mmol) in 1,4-dioxane (6 mL) was added N-methyl-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (417 mg, 1.50 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol) and potassium carbonate solution (2 M aqueous, 1.5 mL, 3.0 mmol). The reaction mixture was stirred at 105° C. for 3 h and was then cooled to rt. EtOAc and H2O were added. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude mixture was purified by CombiFlash (EtOAc/Hex) to give (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(4-(methylamino)-3-nitrophenyl)benzo[d]thiazol-6-yl)acetate. 1H NMR (400 MHz, CD3OD):δ 8.71 (s, 1H), 8.40 (m, 1H), 8.05 (dd, J=8.8, 2.4 Hz, 1H), 7.73 (s, 1H), 7.51-7.58 (m, 4H), 7.06 (d, J=8.8 Hz, 1H), 5.22 (s, 1H), 4.22 (m, 2H), 3.05 (d, J=4.8 Hz, 3H), 2.55 (s, 3H), 1.22 (t, J=7 Hz, 3H), 0.97 (s, 9H).
