Phthalimide → Tert-butyl (2-((4-cyanophenyl)amino)-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyridin-4-yl)(propyl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl (2-((4-cyanophenyl)amino)-5-(5-hydroxy-1-pentyn-1-yl)pyridin-4-yl)(propyl)carbamate (S11, 17 mg), phthalimide (12 mg) and triphenylphosphine (21 mg) in tetrahydrofuran (1 mL), a 2.2 mol/mL solution of diethyl azodicarboxylate in toluene (36 μL) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (eluent, 100 to 40% hexane in ethyl acetate) to obtain tert-butyl (2-((4-cyanophenyl)amino)-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyridin-4-yl)(propyl)carbamate (S12, 20 mg).

Provenance & Evidence