反应详情

1-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (9.63 g, 64.6 mmol), tert-butyl(trans-3-hydroxycyclobutyl)carbamate (Intermediate 69, 12.1 g, 64.6 mmol), and triphenylphosphine (25.4 g, 97 mmol) were mixed in THF (250 mL) under an argon atmosphere at 0° C. Diisopropyl azodicarboxylate (19.0 mL, 97 mmol) was added dropwise via syringe, and the reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was diluted with saturated NaHCO3 and extracted with EtOAc (3×). The organic layer was separated, washed with brine, dried over MgSO4, filtered, and concentrated. The resulting crude product was purified via silica gel flash column chromatography eluting with 0 to 100% EtOAc in hexanes to yield the title compound as a yellow solid and used in the next step without further purification.

1. extractionextracted with EtOAc (3×)
2. customThe organic layer was separated
3. washwashed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting crude product was purified via silica gel flash column chromatography
8. washeluting with 0 to 100% EtOAc in hexanes