A suspension of 7-bromo-6-iodo-1,2-benzothiazole (29.6 mg, 0.0871 mmol), 3-fluorobenzeneboronic acid (12.8 mg, 0.0915 mmol), potassium carbonate (39.2 mg, 0.284 mmol), and Pd(PPh3)4 (12.2 mg, 0.0106 mmol) in 4:1 1,4-dioxane:water (1 mL) was heated to 80° C. for 15 h. The reaction mixture was concentrated in vacuo. Purification of the residue by ISCO chromatography (0 to 100% dichloromethane:heptane) to afford 16.2 mg (59%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.08 (s, 1H), 7.73 (d, J=7.58 Hz, 1H), 7.52 (dt, J=5.81, 7.96 Hz, 1H), 7.37 (qd, J=0.88, 7.71 Hz, 1H), 7.33 (d, J=7.58 Hz, 1H), 7.28-7.31 (m, 1H), 7.20 (ddt, J=1.01, 2.59, 8.43 Hz, 1H); MS (ESI): 307.87, 309.86 [M+H]+; HPLC tR=4.33 min (ZQ3: nonpolar—5 min).
