Cesium fluoride → 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-3-vinylimidazo[1,2-a]pyridine

Participants

Reaction Conditions

Reaction Steps

To Example 8 (0.11 g, 0.23 mmol), cesium fluoride (0.14 g, 0.93 mmol) and bis(tri-t-butylphosphine)palladium(O) (18 mg, 0.04 mmol) under nitrogen was added degassed dioxane (2.3 mL) followed by tributyl(vinyl)stannane (0.30 mg, 0.93 mmol). The reaction was heated at 80° C. for 2 h and, after cooling to room temperature, was diluted with EtOAc (10 mL). The organic layer was washed with saturated aqueous sodium carbonate (2×10 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-100% EtOAc/hexanes) to give Example 10. 1H NMR (500 MHz, CDCl3) δ 8.17 (d, J=7.0 Hz, 1H), 7.60 (s, 1H), 7.55 (d, J=9.2 Hz, 1H), 7.21-7.17 (m, 1H), 6.93-6.82 (m, 2H), 5.63 (d, J=18.1 Hz, 1H), 5.43 (d, J=12.1 Hz, 1H), 2.93-2.87 (m, 1H), 2.89 (s, 3H), 2.74-2.70 (m, 1H), 2.67 (s, 3H), 2.39 (s, 3H), 2.00-1.92 (m, 2H) ppm; MS: m/z=372.3 (M+H).

Provenance & Evidence