Cesium carbonate → 3-Cyclopropyl-4-(cyclopropylmethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-Bromo-4-cyclopropylmethoxy-pyridine (Example 42a, 4.1 g, 18.0 mmol) in a mixture of toluene (55 ml) and water (6.5 ml) was added potassium cyclopropyltrifluoroborate (CAN 1065010-87-8, 2.79 g, 18.9 mmol), palladium(II) acetate (80.7 mg, 360 μmol), butyldi-1-adamantylphosphine (CAN 321921-71-5, 193 mg, 539 μmol) and cesium carbonate (14.6 g, 44.9 mmol). The reaction mixture was stirred at 115° C. for 16 h, cooled down to room temperature and filtered through a pad of celite. The filtrate was poured into a separatory funnel, diluted with ethylacetate and extracted with water. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness. The crude was purified by flash chromatography on silica eluting with a heptane/(solution 3% triethylamine in ethylacetate) gradient to yield the title compound (2.67 gr, 78.5%) as a yellow oil. MS (ESI, m/z): 190.3 (M+H+).

Provenance & Evidence