Thiophenol → (S)-tert-Butyl (1-(4-oxo-3-phenyl-5-(phenylthio)-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl (1-(5-iodo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (700 mg, 1.46 mmol) was dissolved in 50 mL dimethylformamide in a pressure reactor. Phenyl hydrosulfide (241 mg, 2.19 mmol), potassium carbonate (302 mg, 2.19 mmol) and copper(I) iodide (416 mg, 2.18 mmol) were added under argon atmosphere and the reaction mixture heated at 70° C. overnight. The reaction mixture was cooled at room temperature and partitioned between ethyl acetate and water. The organic phase was washed with water, brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase using Isolera® Purification System to give 190 mg (28% yield) to the title compound. Purity 100%.

Provenance & Evidence