Cyanide → HCID 86757583, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester (10.0 g, 39.5 mmol) in DMF (50 mL) and ethanol (10 mL) was added either sodium cyanide (3.9 g, 80.0 mmol) or tetrabutylarimonium cyanide (11.8 g, 1.1 eq) or tetrabutylammonium chloride (14.7 g, 1.0 eq) and sodium cyanide (2.4 g, 1.2 eq) together. This solution or suspension was warmed up to 60° C. until reaction was completed as judged by TLC. The reaction mixture was then diluted with water (200 mL) and stirred gently at rt for 10 min. A large amount of precipitate formed. The solid was filtered and rinsed thoroughly with water to afford the title compound as an off-white solid after drying: 40-80% yield. This material was >95% pure as judged by HPLC and was used directly without further purification.

Provenance & Evidence