Potassium Carbonate → ethyl 9-(cyanomethyl)-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 6,7-dihydro-5H-cyclopenta[c]pyridin-7-ylacetonitrile (90.0 mg, 0.569 mmol) in acetonitrile (1.0 mL) was added 1-(aminooxy)-2,4-dinitrobenzene (113 mg, 0.567 mmol), and the mixture was stirred at 40° C. for 12 hr. The solvent was evaporated under reduced pressure. The residue was dissolved in dimethylformamide (1.0 mL), ethyl 2-butynoate (80.0 μL, 0.686 mmol) and potassium carbonate (94.4 mg, 0.683 mmol) were added, and the mixture was stirred at room temperature for 4 hr. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (51.2 mg, yield 32%).

Provenance & Evidence