Cesium carbonate → HCID 86712642, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(2-((2-chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)acetate (K7) (100 mg, 0.333 mmol) in 1,4-dioxane (8 mL) was added tert-butyl 4-(5-aminopyridin-2-yl)piperidine-1-carboxylate (K4) (92.2 mg, 0.333 mmol), Cs2CO3 (433 mg, 1.33 mmol), Pd2(dba)3 (30 mg, 0.033 mmol) and Xantphos (58 mg, 0.10 mmol). The resulting mixture was degassed with nitrogen for 5 minutes before heating under microwave irradiation for 30 minutes at 120° C. The resulting mixture was diluted with EtOAc (100 mL) then washed with water (2×25 mL), brine (25 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-100% EtOAc in hexanes) to give the title compound A17 as a yellow foam (112 mg, 62%); 1H NMR (400 MHz, CDCl3) δ 8.62 (d, J=2.4 Hz, 1H), 8.32 (d, J=0.6 Hz, 1H), 8.16 (dd, J=8.5, 2.7 Hz, 1H), 7.66 (dd, J=7.6, 0.9 Hz, 1H), 7.43-7.30 (m, 3H), 7.14 (d, J=8.5 Hz, 1H), 7.10 (s, 1H), 4.25 (br. s, 2H), 3.95 (s, 2H), 3.70 (s, 3H), 2.86-2.78 (m, 3H), 2.35 (d, J=0.4 Hz, 3H), 1.91 (d, J=13.3 Hz, 2H), 1.75-1.63 (m, 2H), 1.47 (s, 9H). LCMS-A: rt 5.462 min; m/z 542 [M+H]+.

Provenance & Evidence