Dimethylformamide → Quinoline-7-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 7-quinolinyl trifluoromethanesulfonate (1.88 g, 6.8 mmol) in DMF (40 ml) was degassed for 10 minutes with Argon. Zinc(II) cyanide (0.48 g, 4.08 mmol), tris(dibenzylideneacetone)dipalladium(0) (155 mg, 2.5% mmol) and 1,1′-bis(diphenylphospino)ferrocene (188 mg, 5% mmol) was then added and the mixture was heated at 100° C. under argon for 1.5 h. The solvent was evaporated and residue dissolved in DCM and organic phase washed with a saturated solution of sodium bicarbonate. The aqueous phase was extracted with DCM (3×80 ml). The combined organic phases were dried, evaporated and the residue was chromatographed on silica gel, eluting with 0-10% methanol-DCM to afford the desired compound (1.01 g, 97%).

Provenance & Evidence