(S)-tert-butyl 1-(3-bromo-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethylcarbamate → tert-Butyl (S)-(1-(5-amino-3-bromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Participants

Reaction Steps

To a mixture of (S)-tert-butyl (1-(3-bromo-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate (30E, 1.5 g, 2.7 mmol) in 27 ml of ethanol, 0.9 ml of hydrazine monohydrate was added and stirred at room temperature for 2 hours. To the reaction mixture, ethanol was added and filtrated, and the filtrate was concentrated. The residue was diluted with ethyl acetate, and washed with water and then with a saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give the title product. MS (m/z) 427.83 [M+H]+.

Provenance & Evidence