Dimethylformamide → HCID 59594537, compound

Participants

Reaction Conditions

Reaction Steps

To a 200 mL round bottom flask was added 5-chloro-3-fluoro-4-iodopyridin-2-amine (9.7 g, 5.5 mmol, 1.0 equiv), zinc cyanide (4.6 g, 6.1 mmol), tetrakis(triphenylphosphine)palladium(0) (4.1 g, 0.56 mmol), and DMF (80 mL). The reaction mixture was heated to 175° C. for 40 minutes. The reaction was then poured into a mixture of EtOAc (300 mL) and brine (150 mL). The organic layer was separated, washed with brine (150 mL), dried over Na2SO4, and concentrated. The residue was dissolved in CH2Cl2 and purified by silica gel chromatography (5-30% EtOAc/hexanes) to yield 4.1 g of the title compound (69%) as an off-white solid.

Provenance & Evidence