Water → HCID 66837119, compound

Participants

Reaction Steps

A vial was charged with tetrakis(triphenylphosphine)palladium(0) (0.129 g, 0.112 mmol), 4-bromo-1H-benzo[d]imidazole (0.200 g, 1.015 mmol), sodium carbonate (0.430 g, 4.06 mmol), and 4-methylpyridin-3-ylboronic acid (0.146 g, 1.066 mmol). The mixture was stirred at room temperature for 10 min under N2, then water (1.894 mL), DME (3.79 mL), and EtOH (1.894 mL) were added sequentially. The resultant mixture was stirred under N2 for 15 min, then heated at 90° C. overnight. After 21.5 h, the reaction mixture was allowed to cool to room temperature, then quenched with water and diluted with EtOAc. The layers were separated and the aqueous phase extracted with EtOAc (3×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford a brown residue. The crude material was dissolved in a minimal amount of CH2Cl2 and chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (40 g column, 40 mL/min, 1-20% MeOH in CH2Cl2 over 30 min, tr=20 min) gave the title compound (132 mg, 0.631 mmol, 62.1% yield) as a white foam. ESI MS (M+H)+=210.0. HPLC Peak tr=14.20 minutes. Purity >99%. HPLC conditions: Xbridge Phenyl column, 4.6×150 mm. 30 min gradient (10-100% B), 2 mL/min, 23° C. @ 220 nm, Solvent A: 10 mM NH4HCO3 pH 9.5 in H2O:MeOH (95:5), Solvent B: 10 mM NH4HCO3 pH 9.5 in H2O:MeOH (5:95).

Provenance & Evidence