Dimethylformamide → HCID 57978000, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 6-chloro-5-(4-chlorophenyl)-4-(pyridinyl)pyridazin-3-ol (1.1 gm, 3.47 mmol), DMF (10 ml), K2CO3 (0.958 gm, 6.94 mmol), and 3-(chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine (0.798 gm, 3.817 mmol). The reaction was heated to 80° C. and stirred at that temperature for 2 hrs. The reaction was then cooled to rt and diluted with EtOAc (75 ml). The resulting mixture was poured into a separatory funnel, washed with water (4×10 ml) and with saturated aqueous NaCl (15 ml). The organic layer was then slurried with MgSO4 to remove excess water, filtered and concentrated. The crude product was purified using an automated column chromatography system (ISCO, 40 gm silica gel) eluting with a gradient of 40%-100% EtOAc/Hex to give product 6-chloro-5-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one as beige solid (1.35 gm, 79% yield). HPLC retention time (method A)3.140 min; LCMS (M+H)=491.1.

Provenance & Evidence