Trimethylsilyl cyanide → 1H-Pyrazolo[4,3-b]pyridine-5-carbonitrile

Participants

Reaction Steps

To a solution of 4-hydroxy-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazolo[4,3-b]pyridinium (1.59 g, 6 mmol) in DCM (130 mL) was added TMSCN (1.13 mL, 9 mmol). After 5 min at rt, (Me)2N(C(O)Cl (0.83 mL, 9 mmol) was added. The reaction mixture was stirred at rt for 4 days, after which it was diluted with DCM, washed with brine, and dried. Concentration followed by purification through column afforded 1H-pyrazolo[4,3-b]pyridine-5-carbonitrile (1 g, 61%).

Provenance & Evidence