Sodium Carbonate → 1,1-Dimethylethyl (2S)-4-({4-[{[6-(3-fluorophenyl)-2-pyridinyl]carbonyl}(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,1-dimethylethyl (2S)-4-({4-[[(6-chloro-2-pyridinyl)carbonyl](methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate (D107) (0.0825 g, 0.179 mmol), 3-fluorobenzeneboronic acid (0.0302 g, 0.216 mmol), tetrakis-(triphenylphosphine)palladium (0) (0.0104 g, 0.009 mmol) and sodium carbonate (0.0762 g, 0.719 mmol) in a DME/water (4 mL, 1:1) was heated at 140° C. in a microwave for 10 minutes. The reaction mixture was diluted with DCM/water and the aqueous layer was further extracted with DCM (×3). The combined organics were dried and concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% EtOAc/hexane gave the title compound as a colourless oil (0.0781 g). MS (ES): MH+ 519.3.

Provenance & Evidence