Potassium Carbonate → HCID 58387200, compound

Participants

Reaction Conditions

Reaction Steps

A 4 mL vial with a septum cap and a stirring bar was charged with phenylboronic acid (4.5 mg, 0.037 mmol) and Pd(PPh3)4 (2.0 mg, 5 mol %) and was purged briefly with N2. A solution of 3-(5-bromo-6-chloro-1H-benzimidazol-2-yl)-propionic acid methyl ester (Intermediate 9, 10.0 mg, 0.032 mmol) in DME (200 uL) was added to the vial, followed 1M aqueous K2CO3 (100 uL). The resulting mixture was stirred at 85° C. for 10 h. The mixture was allowed to cool down to rt, and was partitioned with EtOAc (1 mL) and 10% aqueous AcOH (1 mL). The organic layer was separated and evaporated to dryness in vacuo. The resulting oily residue was dissolved in DMSO (1.0 mL), filtered and purified by reverse-phase HPLC to give the title compound. LR-MS (API-ES): calculated for C16H13ClN2O2 300.0, observed m/e 301.0 (M+H)+ (Rt 2.42 min).

Provenance & Evidence