Water → HCID 68454714, compound

Participants

Reaction Conditions

Reaction Steps

(R)-3-Methylmorpholine (93 mg, 919 μmol) was dissolved in p-xylene (0.460 mL) before 6-bromo-1-chlorophthalazine (112 mg, 460 μmol) was added. The reaction mixture was heated to 165° C. for 1.5 h, then diluted with ethyl alcohol (4.61 mL) before N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (153 mg, 507 μmol), tetrakis(triphenylphosphine)palladium (27 mg, 23 μmol), and potassium carbonate—1.5 M in water (1229 μl, 1843 μmol) were added. The mixture was heated to 90° C. for 1 h, diluted with 50 mL of ethyl acetate, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2 times with 20 mL of sodium bicarbonate (saturated, aqueous) and separated. The organic layers were dried over sodium sulfate, concentrated, and purified by flash chromatography to give the title compound. MS (ES+): 403(M+H)+.

Provenance & Evidence