Sodium Carbonate → 2-benzyl-4-methoxy-5-p-tolylpyridazin-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-benzyl-5-chloro-4-methoxypyridazin-3(2H)-one (20 g, 80 mmol), prepared as described in Example 361B, and 4-methylphenylboronic acid (13 g, 96 mmol) in toluene (300 mL) at RT under argon was added (Ph3P)4Pd (1.85 g, 1.8 mmol) and 2 M aqueous Na2CO3 solution (160 mL, 320 mmol). The resulting suspension was heated at 100° C. for 5 h with stirring. HPLC/MS indicated complete reaction. After cooling the reaction mixture to room temperature, it was extracted with CH2Cl2 (200 mL×2), then dried (Na2SO4), filtered and concentrated under vacuum. The crude product was purified by silica gel column chromatography (ISCO) eluting with hexanes/EtOAc to give the title compound, 2-benzyl-4-methoxy-5-p-tolylpyridazin-3(2H)-one, (21.9 g, 89%) as a white foam. MS [M+H]+ 307; HPLC retention time=3.78 min.

Provenance & Evidence