反应详情

温度

0 °C

1-Cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.740 g, 4.22 mmol), benzyl (trans-3-hydroxycyclobutyl)carbamate (0.934 g, 4.22 mmol), and triphenylphosphine (1.661 g, 6.33 mmol) were mixed in THF (15 mL) under an argon atmosphere and cooled to 0° C. Diisopropyl azodicarboxylate (1.244 mL, 6.33 mmol) was added dropwise via syringe, and the reaction mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and extracted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with EtOAc in hexanes to yield benzyl (trans-3-(1-cyclopropyl-2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)cyclobutyl)carbamate (1.244 g, 3.29 mmol, 78% yield) as an off-white solid. M+1: 379.2.

1. temperaturethe reaction mixture was warmed to room temperature
2. extractionextracted with EtOAc
3. customThe organic layer was separated
4. washwashed with saturated aqueous sodium chloride
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting crude product was purified by silica gel column chromatography
9. washeluting with EtOAc in hexanes