Methanol → 6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid methyl ester

Participants

Reaction Steps

To a stirred solution of 3-butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazine (Example 14, 29 mmol, 10.0 g) in mixture of methanol and DMF (1:1, 100 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) PdCl2 (10 mol %, 2.2 g), DPPF (10 mol %, 1.6 g) and TEA (72.5 mmol, 10 mL). The reaction was stirred at 90° C. under 40-50 psi pressure of carbon monoxide for 8 h. The solvent was removed, and the crude product was purified using hexane:ethyl acetate on a 330 g ISCO silica gel column to provide 6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid methyl ester (10.0 g).

Provenance & Evidence