Water → 4-Methyl-3-{1-[(3R)-3-methylmorpholin4-yl]phthalazin-6-yl}benzamide

Participants

Reaction Conditions

Reaction Steps

To (R)-3-methylmorpholine (108 mg, 1068 μmol) and 6-bromo-1-chlorophthalazine (130 mg, 534 μmol) was added p-xylene (534 μl) and the mixture was heated to 165° C. for 1.5 h. The reaction mixture was added to 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (154 mg, 589 μmol), tetrakis(triphenylphosphine)palladium (31 mg, 27 μmol), ethanol (5.35 mL), and potassium carbonate—1.5 M in water (1428 μl, 2142 μmol) and heated to 90° C. for 1 h. It was cooled to RT, diluted with 50 mL of ethyl acetate, partitioned with sodium bicarbonate (saturated, aqueous), and the organics were washed 2×20 mL with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to give the title compound.

Provenance & Evidence