Triphenylphosphine → HCID 178454104, compound

Participants

Reaction Steps

5-Bromo-3,3-difluoro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (1.19 g, 4.78 mmol), tert-butyl(cis-3-hydroxycyclobutyl)carbamate (0.895 g, 4.78 mmol), and triphenylphosphine (1.88 g, 7.17 mmol) were mixed in THF (18 mL) under an argon atmosphere. The mixture was cooled to 0° C. before diisopropyl azodicarboxylate (1.409 mL, 7.17 mmol) was added dropwise via syringe. The reaction mixture was warmed to room temperature and stirred for 19 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 via silica gel column chromatography eluting with EtOAc in hexanes to yield the title compound (0.477 g, 1.141 mmol, 23.9% yield) as a white solid.

Provenance & Evidence