Cesium carbonate → HCID 90067636, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-chloro-6-(3,3-difluoropyrrolidin-1-yl)-4-(3-pyridyl)pyridine (2-b, 63 mg, 0.2131 mmol), 2-amino-4-(trifluoromethyl)PYRIDINE (70 mg, 2.0 equiv., 0.4261 mmol), XantPhos (25 mg, 0.20 equiv., 0.04261 mmol), Pd2(dba)3 (20 mg, 0.10 equiv., 0.02131 mmol) in 1,4-dioxane (2.4 mL, 130 equiv., 27.70 mmol) was added cesium carbonate (208 mg, 3.0 equiv., 0.6392 mmol), and the reaction was maintained at 180° C. for 90 min. The crude was diluted with water, and extraction was done with EtOAc. After evaporation of the organic layers, the crude was purified via silica gel chromatography (0-100% EtOAc/Heptane) to 60 mg (67% after two steps) brown solid. 1H NMR (400 MHz, CDCl3) δ (delta) 8.86 (s, 1H), 8.66 (d, J=4.8 Hz, 1H), 8.58 (s, 1H), 8.38 (d, J=5.2 Hz, 1H), 7.89 (d, J=7.9 Hz, 1H), 7.46 (s, 1H), 7.43-7.35 (m, 1H), 7.05 (d, J=5.2 Hz, 1H), 6.55 (s, 1H), 6.10 (s, 1H), 3.93 (t, J=13.1 Hz, 2H), 3.79 (t, J=7.3 Hz, 2H), 2.62-2.47 (m, 2H). LCMS: m/z 422 (M+H).

Provenance & Evidence