Water → HCID 68106705, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of tert-butyl {2-[(3-bromobenzyl)(methyl)amino]-2-oxoethyl}carbamate (293 mg) in toluene (4 ml) were added water (2 ml), (4-chlorophenyl)boronic acid (192 mg), sodium carbonate (173 mg), and tetrakis(triphenylphosphine)palladium (28 mg), followed by stirring at 80° C. overnight. The reaction mixture was cooled to room temperature, and then water was added thereto, followed by extraction with EtOAc. The organic layer was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to ½). The purified product was dissolved in EtOAc (5 ml), and then 4 M hydrogen chloride/EtOAc (10 ml) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and then MeCN was added thereto. The precipitated solid was collected and washed with MeCN to obtain N-[(4′-chlorobiphenyl-3-yl)methyl]-N-methylglycinamide hydrochloride (267 mg).

Provenance & Evidence