Ethanol → HCID 68452315, compound

Participants

Reaction Steps

6-Bromo-1-morpholinophthalazine (405 mg, 1377 μmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (524 mg, 2065 μmol), potassium acetate (541 mg, 5507 μmol), and 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (101 mg, 138 μmol) were dissolved in N,N-dimethylformamide (4.6 mL) and placed in the microwave for 10 min at 160° C. The reaction mixture was added to a vial containing methyl 5-bromo-4-methylthiophene-2-carboxylate (388 mg, 1652 μmol), tetrakis(triphenylphosphine)palladium (159 mg, 138 μmol), potassium carbonate-2 M in water (2754 μl, 5507 μmol), and ethanol (4590 μl, 1377 μmol). The vial was placed in the microwave for 10 min at 160° C., cooled, diluted with 75 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 3× with 50 mL of sodium bicarbonate (saturated, aqueous), and separated. The aqueous layer was acidified to pH 4 with conc. HCl and extracted 3× with 50 mL of chloroform. The combined organic layers were dried over sodium sulfate, and concentrated via rotovap to give a crude product, which was purified by chromatography to obtain the title compound, as the TFA salt. Found MS (ES+): 356(M+H)+.

Provenance & Evidence