Biphenyl-2-boronic acid → 2-biphenyl-2-yl-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

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Reaction Conditions

Reaction Steps

2-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one (50 g, 0.17 mmol), biphenyl-2-ylboronic acid (51.4 mg, 0.26 mmol), and Tetrakis (19.6 g, 0.017 mmol) were added to a flask and purged with N2 (3×). After the addition of toluene (5 mL), ethanol (0.5 mL), and 2M Na2CO3 (0.5 mL) the resulting mixture was heated to 90° C. for 1 hour. The reaction was concentrated in vacuo and the crude residue was dissolved in H2O/EtOAc (1:1) and extracted with H2O, 1N HCl (2×), brine (2×), dried over MgSO4, and concentrated in vacuo to yield an oil. The crude material was purified via silica gel chromatography (CH2Cl2/EtOAc/MeOH) to yield the title compound.

Provenance & Evidence