Potassium Carbonate → 2-{1-[Tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}-1,3-thiazole

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid (0.274 g, 0.46 mmol, based on presumed 45% yield of previous step), 2-bromo-1,3-thiazole (0.206 g, 1.2 mmol), potassium carbonate (0.1736, 1.2 mmol), tetrakis(triphenlyphosphine)palladium(0) (0.040 g, 0.035 mmol) in mixed solvent of benzene/water/methanol (10 mL/1 mL/1 mL), was degassed for 5 minutes, then refluxed at 90° C. for overnight. The reaction mixture was quenched with H2O (30 mL), then extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica gel using an ISCO single channel system (Hexane/EtOAc=9/1 to 1/9) to afford 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]-1,3-thiazole as a yellow oil.

Provenance & Evidence