Sodium Bicarbonate → tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Participants

Reaction Steps

A solution of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.279 g, 0.67 mmol) and 8-methoxyquinoline-2-carbaldehyde (0.125 g, 0.67 mmol) in EtOH (10 mL) was stirred at ambient temperature for 18 hours. The solvent was removed under reduced pressure. The residue was dissolved in DCM (10 mL) and iodobenzene diacetate (0.259 g, 0.80 mmol) was added. The mixture was stirred at ambient temperature for 2 hours. Ethyl acetate (20 mL) and saturated sodium bicarbonate (10 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by flash chromatography on silica gel (20:1 ethyl acetate/MeOH) to give tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.140 g, 38.6%) as a solid.

Provenance & Evidence