Triphenylphosphine → N-(5-Ethenyl-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

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A solution of N-(5-bromo-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D78, 800 mg, ˜75% purity) and n-tributylvinyltin (0.697 ml, 2.3 mmol) in toluene (30 ml) was treated, under a positive flow of argon, with triphenylphosphine (129.8 mg, 0.5 mmol) and bis(dibenzylideneacetone)palladium(0) (170.1 mg, 0.297 mmol), then stirred and heated under argon atmosphere at 130° C. for 1.5 h. The mixture was filtered through a celite pad. The organic layer was washed with NH4OH (10% aq) and water, then dried over MgSO4 and concentrated. The mixture was purified on silica column (100 g of silica, methanol/dichloromethane, 5% to 20%, 15CV) to afford 550 mg of title compound.

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