Diethyl Ether → 3-methyl 1-(phenylmethyl) 4-[3-chloro-4-(trifluoromethyl)phenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-methyl 1-(phenylmethyl) 4-{[(trifluoromethyl)sulfonyl]oxy}-1,3-piperidinedicarboxylate (3 g) (P38) and [3-chloro-4-(trifluoromethyl)phenyl]boronic acid (1.826 g) in dry toluene (37 mL) under N2 atmosphere at 0° C., Pd(PPh3)4 (292 mg) dissolved in absolute EtOH (26 ml), was added followed by Na2CO3 2M (21 mL). The reaction mixture was heated to 80° C. for 2 h. Et2O was then added to the solution and the organic phase was separated. The aqueous layer was extracted with Et2O and the combined organic phases were washed with saturated NaCl aqueous solution, dried and concentrated under vacuum. The crude was purified by flash-chromatography (eluting with cyclohexane/ethyl acetate from 9:1 to 8:2) to give the title compound (3.03 g).

Provenance & Evidence