3,6-Dichloropyridazine → 3-Chloro-6-(4-methoxyphenyl)pyridazine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxyphenylboronic acid (3 g, 0.02 mol) and 3,6-dichloro-pyridazine (3.58 g, 0.024 mol) in 2 M Na2CO3/EtOH toluene (40 mL/20 mL/100 mL) was bubbled through N2 for 5 min. Pd(PPh3)4 (1.15 g, 0.001 mol) was added under N2 and the reaction was heated to 80° C. for 16 h. The mixture was diluted with 100 mL of EtOAc and 20 mL of water. The organic phase was separated, washed with 50 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid obtained was washed with 50% EtOAc/hexane to provide the title compound as off-white solid. MS (ESI pos. ion) m/z: 221.0 (M+H). Calc'd Exact Mass for C11H9ClN2O: 220.65.

Provenance & Evidence