Ethyl Acrylate → Ethyl-3-[3-[[2-methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]phenyl]carbamoyl]phenyl]prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-N-[2-methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]phenyl]benzamide (0.442 g, 0.8 mmol), ethyl acrylate (0.872 mL, 8 mmol), palladium(II) acetate (9 mg, 0.04 mmol), tri(o-tolyl)phosphine (0.049 g, 0.16 mmol) in DMF (4.6 mL) and HMPA (0.4 mL) is added DIPEA (0.557 mL, 3.2 mmol). The mixture is degassed with N2 then sealed and heated at 100° C. for 15 hours. The reaction is not complete, and is stirred at 100° C. for another 24 hours. The mixture is poured into saturated aqueous NaHCO3 and extracted with EtOAc (2×). Organic layers are combined, dried and concentrated to give the title compound as a solid (485 mg), which is used without further purification. LCMS (m/z)=572.5 [M+H]+, tR=3.14 min.

Provenance & Evidence