Trimethylsilyl cyanide → (2-Ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)acetonitrile

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Reaction Steps

Under an argon atmosphere, to a solution of boron trifluoride diethyl ether complex (0.563 mL, 4.44 mmol) and trimethylsilyl cyanide (0.789 mL, 5.92 mmol) in chlorobenzene (30 mL) was added a solution of (2-ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol (340 mg, 1.48 mmol) in chlorobenzene (15 mL) under ice-cooling, and the mixture was stirred at room temperature for 15 min. A saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (252 mg, yield 71%).

Provenance & Evidence