Water → HCID 59726015, compound

Participants

Reaction Conditions

Reaction Steps

To a 150 mL round-bottomed flask was added 6-bromo-1-chlorophthalazine (18, 357 mg, 1465 μmol), tetrakis(triphenylphosphine)palladium (84.7 mg, 73.3 μmol), 4-methyl-N-(1-methyl-1H-pyrazol-5-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (500 mg, 1465 μmol), sodium carbonate (466 mg, 4396 μmol). The reagents were dissolved in DME:water mixture (15 mL, 4:1). The reaction mixture was stirred at 80° C. for 16 hours. The reaction mixture was evaporated and residue dissolved in ethyl acetate (20 mL) and washed with water (2×20 mL) and dried over MgSO4 and rotovaped to yield the title compound 24 as a crude product. The crude product 24 was adsorbed on silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with a gradient of 65% to 80% EtOAc in DCM, to provide 3-(1-chlorophthalazin-6-yl)-4-methyl-N-(1-methyl-1H-pyrazol-5-yl)benzamide (24).

Provenance & Evidence