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

Temperature

110 °C

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).

1. temperatureThe reaction mixture was cooled to room temperature
2. stirringthe reaction mixture was stirred overnight at 120° C. under argon atmosphere
3. temperatureThe reaction mixture was cooled to room temperature
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with water and saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel chromatography (basic silica gel, methanol/ethyl acetate)

ORD record

ord-b2e7b16a60894d609bc8afdf245d5653

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085578B2