Potassium Carbonate → t-Butyl 2-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Commercially available 1-(t-butoxycarbonyl)pyrrole-2-boronic acid (10.06 g, 47.7 mmol) was dissolved in a mixed solvent of 1,2-dimethoxyethane (150 mL) and water (25 mL), and 2-bromothiazole (4.40 mL, 48.8 mmol), palladium (II) acetate (535 mg, 2.38 mmol), triphenylphosphine (2.50 g, 9.53 mmol) and potassium carbonate (19.50 g, 141 mmol) were added, followed by stirring at 90° C. for 16 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, water (300 mL) and ethyl acetate (400 mL) were added, and the solution was separated. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-20%) to afford the desired compound (6.71 g, yield 56%) as a pale yellow oil.

Provenance & Evidence