Diisopropylethylamine → HCID 86659915, compound

Participants

Reaction Steps

To a suspension of 1-(2-pyridylmethyl)-3,3-dimethylindolin-5-ol dihydrochloride (50.0 mg, 0.15 mmol) in 1 mL of dry tetrahydrofuran was added 4-nitrophenyl chloroformate (34 mg, 0.165 mmol) and diisopropylethylamine (91 μL, 0.52 mmol) under ice-cooled conditions. After the reaction mixture was stirred at room temperature for 1 h, 3-tetrahydrofurylmethylamine (17 μL, 0.165 mmol) and diisopropylethylamine (39 μL, 0.225 mmol) was added with additional stirring overnight. After the reaction mixture was added with water (10 mL), the solution was extracted with ethyl acetate (10 mL). The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50 to 10/90) to obtain the title compound (10.7 mg, 18%) as a white solid having the following characteristics.

Provenance & Evidence