Acetonitrile → HCID 58608107, compound

Participants

Reaction Conditions

Reaction Steps

A resealable tube was charged with 4-chloro-2-iodo-3-phenylfuro[2,3-b]pyridine 6d (0.100 g, 0.281 mmol), 1-(2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)piperidine 201 (0.200 g, 0.576 mmol), sodium carbonate (0.074 g, 0.703 mmol), acetonitrile (4 mL), and water (1 mL). Tetrakis(triphenylphosphine)palladium (0) (0.032 g, 0.028 mmol) was added and the system was purged with argon. The tube was sealed and the mixture stirred at 80° C. for 23 h. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown oil. Purification via preparative thin layer chromatography (eluting with 95:5:0.5 dichloromethane/methanol/ammonium hydroxide) afforded 4-chloro-2-(3-fluoro-4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-phenylfuro[2,3-b]pyridine 6f as a yellow orange oil. MS (MH+) 451.1; Calculated 450 for C26H24ClFN2O2.

Provenance & Evidence