Dimethylformamide → HCID 58001719, compound

Participants

Reaction Conditions

Reaction Steps

Zn(CN)2 (64.3 mg, 0.548 mmol) and Pd(PPh3)4 (84 mg, 0.073 mmol) were added to a solution of 5,6-dichloro-3-pyridinemethanol (130 mg, 0.730 mmol) in anhydrous DMF (1.5 ml) under N2 and the mixture was heated at 95° C. overnight. Low conversion was observed by HPLC. After heating under reflux for 2 h, the conversion did not increase, so additional Pd(PPh3)4 (84 mg, 0.073 mmol) was added. Two more h under reflux gave full conversion. TBME, and 10% Na2CO3 were added. Extraction, drying (MgSO4), filtration, and removal of the solvent afforded the crude product. Purification by flash chromatography using Flashmaster II, a 5 g spherical silica gel cartridge, and mixtures of hexane and EtOAc as an eluent afforded 3-chloro-5-(hydroxymethyl)-2-pyridinecarbonitrile (34.6 mg, 0.205 mmol, 28% yield) as a pale yellow solid.

Provenance & Evidence