Potassium Carbonate → HCID 57654580, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,6-dichloro-pyridazine (1.06 g, 6.98 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (1.47 g, 5.0 mmol) in 2.0 M potassium carbonate (10 mL, 20 mmol) and 1,4-dioxane (40 mL) was degassed by house vacuum for 15 min followed by bubbling with argon for ˜10 min, Peppsi-ipr (340 mg, 0.5 mmol) was then added. After flushing with argon for another ˜10 min, the mixture was heated at 70° C. for 4 h and allowed to cool to room temperature. The solid was removed by filtration through Celite, and the filtrate was separated. The aqueous solution was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, concentrated, and purified by column to provide 0.65 g desired product (46%). 1H NMR (DMSO) δ 9.08 (s, 1H), 8.47 (s, 1H), 8.31 (d, J=9.0 Hz, 1H), 8.01 (d, J=9.0 Hz, 1H), 1.59 (s, 3H); MS (ES) m/z 280.8(M+H+).

Provenance & Evidence