Dichloromethane → {4-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-1H-pyrazol-1-yl}acetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine (0.20 g, 0.44 mmol), ethyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetate (Aldrich, Cat. No. 683566) (0.14 g, 0.49 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (18 mg, 0.022 mmol), and potassium carbonate (0.184 g, 1.33 mmol) in 1,4-dioxane (10 mL) and water (5 mL) was degassed and recharged with nitrogen three times. The reaction mixture was stirred at 85° C. for 6 h. The reaction mixture was adjusted to pH˜4 with 1N HCl. The precipitates formed were filtered, washed with water and ether, and dried under vacuum to afford the desired product (0.10 g, 50%). LCMS (M+H)+=448.0/450.0.

Provenance & Evidence