Sodium Carbonate → HCID 59177759, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [4-(methylthio)phenyl]boronic acid (16.8 mg, 0.1 mmol) and 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (36 mg, 0.10 mmol), Pd(PPh3)4 (5 mg, 0.004 mmol), 2M Na2CO3 (1 mL) and DME (1 mL) was heated at 80° C. overnight. The reaction was cooled to ambient temperature, transferred onto a 1 mL Varian Chem Elut column, eluted with EtOAc, and the filtrate concentrated. The crude product was purified by reverse-phase preparative HPLC using a MeOH:H2O gradient (20:80 to 100:0) with 0.1% formic acid as a modifier to afford the title compound (7.4 mg, 12%). LRMS (ESI), m/z 422 (M+Na).

Provenance & Evidence