Cesium carbonate → (E)-4-Methyl-6-(prop-1-enyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

6-bromo-4-methylpyridin-2-amine (500 mg, 2.67 mmol), (E)-6-methyl-2-(prop-1-enyl)-1,3,6,2-dioxazaborocane-4,8-dione (1.05 g, 5.35 mmol), cesium carbonate (2.61 g, 8.02 mmol) and tetrakis(triphenylphosphine)palladium (0) (309 mg, 267 μmol) were combined with dioxane (7.4 mL and water (1.5 mL) and the mixture was heated to 150° C. for 60 min in the microwave. The reaction mixture was cooled and then diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with water and brine. The organic phase was concentrated in vacuo and then purified by chromatography (silica, 20% to 60% ethyl acetate in hexanes) to give a residue that was triturated with methanol to obtain a yellow precipitate. This precipitate was collected by filtration and dried to give (E)-4-methyl-6-(prop-1-enyl)pyridin-2-amine (235 mg, 1.59 mmol, 59%) as a yellow oil. MS (EI/CI) m/z: 148.8 [M+H].

Provenance & Evidence