Ethyl Acetate → 3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 3,6-dichloropyridzine (Aldrich, 297 mg, 2.0 mmol), 1-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (499 mg, 2.4 mmol), 2 M Na2CO3 (4 mL) and dioxane (4 mL). Argon was bubbled through the reaction for 60 seconds followed by the addition of Tetrakis(triphenylphosphine)palladium (0) (231 mg, 0.2 mmol). The reaction was heated to 80° C. overnight followed by aqueous work up using EtOAc and brine. The organic layer was dried (MgSO4) and concentrated in vacuo followed by column chromatography purification (20% Ethyl Acetate in Hexanes) resulting in the title compound as a white solid (183 mg, 47%). 1H-NMR (CD3OD): δ 8.23 (1H, s), 8.08 (1H, s), 7.84 (1H, br s), 7.34 (1H, br s), 4.00 (3H, s).

Provenance & Evidence