Water → N-(2-methoxy-5-(trifluoromethyl)phenyl)-4-methyl-3-(1-morpholinophthalazin-6-yl)benzamide

Participants

Reaction Steps

3-Iodo-N-(2-methoxy-5-(trifluoromethyl)phenyl)-4-methylbenzamide (205 mg, 471 μmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (34 mg, 47 μmol), bis(pinacolato)diboron (179 mg, 707 μmol), and potassium acetate (118 μL, 1884 μmol) were dissolved/suspended in dimethylformamide (2.4 mL) and placed in the microwave at 160° C. for 10 min. The reaction mixture was then transferred to another vial containing 6-bromo-1-morpholinophthalazine (125mg, 424 μmol), tetrakis(triphenylphosphine) palladium(0)(54 mg, 47 μmol), potassium carbonate-2 M in water (942 μL, 1884 μmol), and ethanol (2.4 mL). The combined mixture was reacted in a microwave oven at 160° C. for 10 min. The reaction mixture was diluted with 50 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 3 times with 50 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated via rotovap to give a crude product. The crude product was purified by chromatography to obtain the title compound. Found MS (ES+): 523(M+H)+.

Provenance & Evidence