Cesium carbonate → HCID 86712718, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(2-((2-chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)acetate (K7) (0.200 g, 0.665 mmol) in 1,4-dioxane (8 mL) was added 1-methyl-1H-pyrazol-4-amine (0.065 g, 0.665 mmol), Cs2CO3 (0.867 g, 2.66 mmol), Pd2(dba)3 (0.061 g, 0.067 mmol) and Xantphos (0.115 g, 0.200 mmol). The resulting mixture was degassed with nitrogen for 5 minutes before heating under microwave irradiation for 30 minutes at 120° C. The mixture was diluted with EtOAc (100 mL), washed with water (2×25 mL), brine (25 mL), dried (Na2SO4) and concentrated under reduced pressure. The resulting brown oil was purified by silica gel column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-100% EtOAc in hexanes) to give the title compound A115 as a yellow solid (0.128 g, 53%); 1H NMR (400 MHz, d6-DMSO) δ 9.47 (s, 1H), 8.39 (s, 1H), 7.89 (s, 1H), 7.67 (d, J=7.4 Hz, 1H) 7.51-7.44 (m, 3H), 7.43-7.37 (m, 1H), 3.98 (s, 2H), 3.81 (s, 3H), 3.61 (s, 3H), 2.25 (s, 3H). LCMS-A: rt 5.856 min; m/z 362 [M+H]+.

Provenance & Evidence