Sodium Bicarbonate → HCID 178451919, compound

Participants

Reaction Conditions

Reaction Steps

A flask charged with PdCl2(dppf) (0.04 g, 0.051 mmol), sodium bicarbonate (0.37 g, 4.45 mmol), and (5)-tert-butyl 2-(3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate (compound 16a, 0.50 g, 1.27 mmol) was flushed with nitrogen. A solution of (S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (compound 20a, 0.67 g, 1.52 mmol) in 1,2-dimethoxyethane (15 ml) was then added. The reaction mixture was stirred at 80° C. under nitrogen for 6 hours. After cooled to room temperature, the resulting mixture was extracted with ethyl acetate/water, dried over magnesium sulfate, filtered and concentrated to give a crude compound, which was purified with chromatography (ethyl acetate: n-hexane=4:1) to yield product 23a as a white solid (0.57 g).

Provenance & Evidence