Cesium carbonate → Tert-butyl 2-(2,6-dimethylpyridin-4-ylamino)propylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-Chloro-2,6-dimethylpyridine (131 mg, 0.925 mmol), tert-butyl 2-aminopropylcarbamate hydrochloride (151 mg, 0.717 mmol), cesium carbonate (750 mg, 2.302 mmol), and anhydrous 1,4-dioxane (3 ml) was treated with tris(dibenzylideneacetone)dipalladium(0) (39 mg, 0.043 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (74 mg, 0.128 mmol) under an atmosphere of argon. The mixture was heated at 110° C. for 8 hours, allowed to reach room temperature and filtered. The filter residue was washed with DCM, the combined filtrates were evaporated. The residue was purified by column chromatography using a gradient of methanol (1-10%) in dichloromethane to yield 241 mg of a yellow oil. MS (ESI) m/z=280.2.

Provenance & Evidence