Water → 4-chloro-N-cyclopropyl-3-(1-morpholinophthalazin-6-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

4-Chloro-N-cyclopropyl-3-iodobenzamide (190 mg, 591 μmol), potassium acetate (174mg, 1773 μmol), bis(pinacolato)diboron (165 mg, 650 μmol), and 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (43 mg, 59 μmol) were suspended in dioxane (3.9 mL) and placed in the microwave for 10 min at 180° C. before being added to a mixture of 6-bromo-1-morpholinophthalazine (120 mg, 408 μmol), sodium carbonate-2 M in water (1.2 mL, 2.4 mmol), tetrakis(triphenylphosphine)palladium (68 mg, 59 μmol), and ethyl alcohol (3.9 mL). The combined mixture was heated in the microwave for 10 min at 180° C. The reaction mixture was diluted with 20 mL of EtOAc, added to an addition funnel, and partitioned with sodium bicarbonate (saturated, aqueous). The organic layers were combined, washed 3 times with 20 mL of sodium bicarbonate (saturated, aqueous), separated, combined, dried over sodium sulfate, and concentrated via rotovap to give a crude product. After purification by chromatography, the title compound was obtained. Found MS (ES+): 409 (M+H)+.

Provenance & Evidence