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

関与物質

反応手順

To a solution of 2-[(aminooxy)sulfonyl]-1,3,5-trimethylbenzene (about 16.4 mmol) in acetonitrile (80 mL) was added a solution of 6,7-dihydro-5H-cyclopenta[c]pyridin-7-ylacetonitrile (1.30 g, 8.22 mmol) in acetonitrile (40 mL), and the mixture was stirred at room temperature for 30 min. N,N-Dimethylformamide (40 mL) was added, and the mixture was concentrated under reduced pressure. To 46% of the residual solution were added methyl 3-phenylpropiolate (671 μL, 4.55 mmol) and potassium carbonate (1.31 g, 9.48 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75) to give the title compound (523 mg).

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