Potassium Carbonate → HCID 131735153, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl(7-iodo-5-methylpyrazolo[1,5-a]pyridin-3-yl)methanone (300 mg), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(triisopropylsilyl)oxazole (330 mg), tetrakis(triphenylphosphine)palladium(0) (90 mg) and 3N aqueous potassium carbonate solution (0.522 mL) in DME (3 mL) was stirred with microwave irradiation at 120° C. for 30 min. The reaction mixture was diluted with saturated aqueous ammonium chloride solution, and 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 column chromatography (NH, ethyl acetate/hexane) to give (5-methyl-7-(2-(triisopropylsilyl)-1,3-oxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)((1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl)methanone. The obtained (5-methyl-7-(2-(triisopropylsilyl)-1,3-oxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)((1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl)methanone was dissolved in THF (3 mL), and 1N hydrochloric acid was added thereto. The reaction mixture was stirred at room temperature for 30 min, saturated aqueous ammonium chloride solution 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 column chromatography (NH, ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (83 mg).

Provenance & Evidence