Triphenylphosphine → HCID 178523831, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence