4-(4-Iodobenzyl)pyridine → (2E)-N-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(pyridin-4-ylmethyl)phenyl]acrylamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-iodobenzyl)pyridine (129 mg, 0.44 mmol), TEA (67 μL, 0.48 mmol), Pd(PPh3)4 (254 mg, 0.222 mmol) and N-[4-chloro-3-(trifluoromethyl)-phenyl]acrylamide (0.120 g, 0.44 mmol) in DMF (4.4 mL) was heated at 95° C. for 3 h. The reaction mixture was cooled to rt, diluted with water, extracted with EtOAc, washed with brine, dried over NaSO4, filtered and concentrated. The residue was purified by column chromatography to give the title compound (161 mg, 40%). LCMS: (FA) ES+ 417.2 (M+1).

Provenance & Evidence