Toluene → HCID 59393682, compound

Participants

Reaction Conditions

Reaction Steps

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (700 mg, 0.960 mmol) was added to a stirred solution of 4a (2.20 g, 4.80 mmol), 3,6-dichloropyridazine (1.40 g, 5.80 mmol) and sodium carbonate (4.80 mL of a 2.0 M aqueous solution, 9.60 mmol) in EtOH:toluene (25.0 mL of an 80:20 mixture, respectively) at rt. The resulting solution was heated to 95° C. for approximately 2 h. After cooling to rt, the reaction mixture was filtered through a short column of CELITE®, eluting with EtOAc. The filtrate was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-60% EtOAc/hexanes as eluent) to furnish the title compound 4b. m/z (ES) 445 (MH)+. 1HNMR (500 MHz, CDCl3): δ 9.19 (d, 1H, J=2.1 Hz), 8.46 (d, 1H, J=1.6 Hz), 8.36 (dd, 1H, J=2.5, 8.5 Hz), 8.29 (d, 1H, J=2.8 Hz), 7.86 (d, 1H, J=8.9 Hz), 7.62 (d, 1H, J=8.9 Hz), 7.52 (m, 4H), 7.46 (d, 1H, J=8.2 Hz), 7.37 (m, 1H), 3.93 (s, 3H), 3.21 (m, 1H), 1.80 (s, 3H), 0.93 (d, 3H, J=6.9 Hz), 0.89 (d, 3H, J=6.9 Hz).

Provenance & Evidence