Sodium Carbonate → HCID 67021267, compound

Participants

Reaction Steps

A mixture of [4-(5-bromo-benzoimidazol-1-yl)-phenyl]-acetic acid ethyl ester (0.300 g, 0.84 mmol), 4-methoxyphenylboronic acid (0.152 g, 1.00 mmol, 1.2 equiv), PdCl2(dppf) (18 mg, 0.025 mmol, 0.03 equiv), Na2CO3 (2 M solution in H2O, 1.7 mL, 3.34 mmol, 4 equiv) in toluene/EtOH (12 mL; 5:1, v/v) is stirred and refluxed for 2 h. After further addition of boronic acid (0.100 g, 0.66 mmol) in EtOH (1 mL), the reaction mixture is stirred and refluxed for 30 min, allowed to cool to rt, diluted with EtOAc and H2O, and filtered through a pad of Celite. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Silica gel column chromatography purification (Hexane/EtOAc, 3:1) provides the title compound as a yellow solid: ES-MS: 387.1 [M+H]+; single peak at tR=4.27 min (System 1); Rf=0.24 (Hexane/EtOAc, 3:1).

Provenance & Evidence