Palladium tetrakistriphenylphosphine (200.0 mg, 0.173 mmol) was added to a stirred suspension of [(3R,3aR,6R,6aS)-3-(1-allyl-6-chloro-5-iodo-imidazo[4,5-b]pyridin-2-yl)oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy-tert-butyl-dimethyl-silane (500.0 mg, 0.865 mmol, Intermediate 5), 4-cyclopropylthiazolo[4,5-c]pyridine (183.0 mg, 1.038 mmol), cesium carbonate (1.409 g, 4.33 mmol), and copper (I) iodide (99.0 mg, 0.519 mmol) in degassed DMF (3.2 mL). The reaction mixture placed under nitrogen before being heated to 100° C. for 3 h. The reaction mixture was cooled to room temperature and added to EtOAc (80 ml). The mixture filtered and the solids washed with EtOAc (2×30 mL). The filtrate was evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 40 g silica RediSep Rf® Gold column and employing a 0-100% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C27H32ClN5O4SSi 585.16 observed m/e: 586.17 (M+H)+ (Rt 1.18/1.8 min)
