2'-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl[1,1'-biphenyl]-2,6-diamine → N-(isoxazol-3-yl)-1-(2-methoxy-5-(tetrahydro-2H-pyran-4-yl)phenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A vial was charged with palladium(ii) acetate (2.83 mg, 0.013 mmol), CPhos (0.011 g, 0.025 mmol) and 1-(5-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.100 g, 0.210 mmol). (Tetrahydro-2H-pyran-4-yl)zinc(II) iodide (0.26M in TI-IF) (2.423 ml, 0.630 mmol) was added and the reaction was stirred at 50° C. for 1 h. The reaction was diluted with ethyl acetate and washed (×2) with 1N HCl solution. The organics were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by reverse-phase preparative HPLC using an XBridge Prep C18 column, 10 micron OBD, 19×100 mm, 0.1% TFA in CH3CN/H2O, gradient 25% to 95% over 12 min to provide N-(isoxazol-3-yl)-1-(2-methoxy-5-(tetrahydro-2H-pyran-4-yl)phenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.039 g, 0.081 mmol, 38.6% yield) as a white solid. m/z (ESI) 482.2 (M+H)+.

Provenance & Evidence