2-Chloropyridine → HCID 66703932, compound

Participants

Reaction Steps

A solution of (2S)-2-(4-aminophenyl)-4-((1R)-1-phenylethyl)morpholine (1.5 g, 5.31 mmol), 2-chloropyridine (1.21 g, 10.6 mmol), tris(dibenzylideneacetone)-dipalladium(0) (52.6 mg, 0.05 mmol), potassium tert-butoxide (0.88 g, 7.8 mmol) and 1,3-bis(2,6-di-i-propylphenyl)imidazolium chloride (89.6 mg, 0.21 mmol) in dioxane (17 ml) was stirred at 90° C. for 15 hours. The solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (hexane-ethyl acetate, 1:2) to afford N-(4-((2S)-4-((1R)-1-Phenylethyl)-morpholin-2-yl)phenyl)pyridin-2-amine (0.68 g, 36%) as red crystals.

Provenance & Evidence