A mixture of 12-bromo-4-iodo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (100 mg, 0.256 mmol), acetimidamide hydrochloride (26.5 mg, 0.282 mmol), Pd(OAc)2 (2.9 mg, 0.0129 mmol), Xantphos (14.8 mg, 0.0256 mmol), and TEA (77.6 mg, 0.768 mmol) in DMF (5 mL) was heated at 40° C. under CO (1 atm) for 2 h. After cooling to room temperature, 2-hydrazinylethanol hydrochloride (57.3 mg, 0.512 mmol) and acetic acid (5 mL) were added. The resulting mixture was heated at 80° C. for 0.5 h. The solvent was removed under reduce pressure and the residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford 2-(5-{12-bromo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-4-yl}-3-methyl-1H-1,2,4-triazol-1-yl)ethan-1-ol (80 mg, 80% yield) as white solid. LCMS (ESI) m/z: 390.1 [M+H+].
