Triethylamine → tert-Butyl 3-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate

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Reaction Conditions

Reaction Steps

A suspension of tert-butyl 3-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate (A78) (500 mg, 1.16 mmol), methyl 2-(2-ethynylphenyl)acetate (K1) (244 mg, 1.39 mmol), Et3N (0.60 mL), PdCl2(PPh3)2 (0.041 g, 0.058 mmol), CuI (0.022 g, 0.117 mmol) and PPh3 (0.031 g, 0.117 mmol) in DMF (4 mL) were heated under microwave irradiation at 120° C. for 15 minutes. The resulting mixture was adsorbed onto silica gel and purified using column chromatography (CombiFlash Rf, 40 g SiO2 cartridge, 0-30% EtOAc in cyclohexane) to give the title compound A79 as a yellow foam (0.570 g, 86%); 1H NMR (300 MHz, d6-DMSO) δ 8.65 (s, 1H), 7.70 (d, J=7.7 Hz, 1H), 7.64 (d, J=8.5 Hz, 2H), 7.48-7.33 (m, 6H), 4.35 (t, J=8.6 Hz, 2H), 4.01-3.96 (m, 4H), 3.75-3.72 (m, 4H), 1.49 (s, 9H). LCMS-B: rt 9.160 min; m/z 567 [M+H]+.

Provenance & Evidence