Cesium carbonate → (S)-tert-butyl 2-(4-(3-chloropyridin-2-ylamino)phenyl)morpholine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 2-(4-aminophenyl)morpholine-4-carboxylate (120 mg, 0.43 mol), 2,3-dichloropyridine (64 mg, 0.43 mmol) and cesium carbonate (211 mg, 0.647 mmol) were combined with dioxane (2 ml) to give a suspension. The mixture was degassed with argon for 5 min. Xanthphos (15 mg, 0.026 mmol) and tris(dibenzylideneacetone)dipalladium chloroform complex (13 mg, 0.013 mmol) were added. The reaction mixture was capped and stirred at 100° C. for 2 h. The crude reaction mixture was filtered through a syringe filter, concentrated in vacuo and purified by flash chromatography (20 g silica gel, 5 to 20% ethyl acetate in heptane) yielded a light yellow foam (88 mg, 53%); MS (ISP): 390.2 ([{35Cl}M+H]+), 392.2 ([{37Cl}M+H]+).

Provenance & Evidence