Cesium carbonate → HCID 86712729, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 2-(2-((2-chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)acetate (K7) (0.100 g, 0.333 mmol), tert-butyl 4-(4-amino-1H-pyrazol-1-yl)piperidine-1-carboxylate (A124) (0.089 g, 0.333 mmol), Cs2CO3 (0.433 g, 1.33 mmol), Pd2(dba)3 (0.030 g, 0.033 mmol) and Xantphos (0.058 g, 0.100 mmol) in 1,4-dioxane (6 mL) 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) and washed with water (2×25 mL), brine (25 mL), dried (Na2SO4) then concentrated under reduced pressure. The resulting brown oil was purified by silica gel column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in hexanes) to give the title compound A125 as a yellow foam (0.096 g, 54%); 1H NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 7.89 (s, 1H), 7.57 (dd, J=7.6, 1.3 Hz, 1H), 7.44 (s, 1H), 7.36-7.22 (m, 2H), 7.19 (s, 1H), 6.87 (s, 1H), 4.22-4.12 (m, 3H), 3.88 (s, 2H), 3.62 (s, 3H), 2.82 (t, J=11.9 Hz, 2H), 2.26 (s, 3H), 2.11-2.02 (m, 2H), 1.89 (qd, J=12.4, 4.4 Hz, 2H), 1.40 (s, 9H). LCMS-A: rt 6.358 min; m/z 531 [M+H]+.

Provenance & Evidence