Potassium Carbonate → HCID 58366265, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 6-chloropyridazine-3-carboxylate (S49, 34 mg, 0.19 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (45 mg, 0.19 mmol), K2CO3 (51 mg, 0.39 mmol), and (Ph3P)4Pd (34 mg, 0.029 mmol) were slurried in DMF (0.3 M). The reaction vessel was evacuated and refilled with argon three times. The mixture was warmed at 85° C. for 16 h. The reaction mixture was cooled and diluted with EtOAc, washed with 9:1 NH4OH:saturated aqueous NH4Cl and saturated aqueous NaCl, and then dried over Na2SO4 Evaporation yielded the crude product that was purified by flash chromatography (SiO2, 1.5×14 cm, 20-100% EtOAc-hexanes) to afford the title compound (25 mg, 53%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 9.03 (d, 1H, J=8.1 Hz), 8.75 (d, 1H, J=8.7 Hz), 8.36 (d, 1H, J=8.7 Hz), 8.09 (t, 1H, J=7.9 Hz), 7.84 (d, 1H, J=7.6 Hz), 4.12 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 164.4, 158.2, 154.4, 151.7, 138.7, 133.9, 129.8, 128.7, 125.5, 125.4, 116.9, 53.6; HRMS-ESI-TOF m/z 241.0721 ([M+H]+, C12H8N4O2 requires 241.0720).

Provenance & Evidence