2,5-Dichloro-4-(2,2,2-trifluoroethoxy)pyridine → 5-Chloro-4-(2,2,2-trifluoroethoxy)picolinonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dichloro-4-(2,2,2-trifluoroethoxy)-pyridine (Example 24a, 1.48 g, 6.02 mmol) in dry DMF (30 mL) under an argon atmosphere was added dicyanozinc (707 mg, 6.02 mmol), 1,1′-bis(diphenylphosphino)ferrocene (267 mg, 481 μmol) and tris(dibenzylideneacetone) dipalladium(0) (275 mg, 301 μmol). The reaction was stirred at 100° C. for 18 h, cooled and filtered through a pad of celite. The filtrate was diluted with ethylacetate and extracted with a 1.0M aqueous solution of sodium bicarbonate. The organic phase was collected and the aqueous solution was back-extracted with ethylacetate. The organic phases were combined, dried over sodium sulfate and evaporated down to dryness. The residue was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (1.04 g, 73%) as a yellow oil. MS (ESI, m/z): 237.3 (M+H+).

Provenance & Evidence