Sodium Carbonate → 3-amino-5-(2-chlorophenyl)-7-(1,3-thiazol-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-7-bromo-5-(2-chlorophenyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one obtained in Step B of Example 18 (200 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (179 mg), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (21.6 mg), potassium acetate (116 mg) and N,N-dimethylformamide (3.0 mL) was stirred overnight at 110° C. under argon atmosphere. The reaction mixture was cooled to room temperature, 4-bromo-1,3-thiazole (0.105 mL), aqueous sodium carbonate solution (2 M, 0.589 mL) and tetrakis(triphenylphosphine)palladium(0) (68.1 mg) were added thereto, and the reaction mixture was stirred overnight at 120° C. under argon atmosphere. The reaction mixture was cooled to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (basic silica gel, methanol/ethyl acetate) to give the title compound (20.0 mg).

Provenance & Evidence