Diethyl Ether → (7-Fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetyl azide

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Reaction Steps

To an ice-cold solution of (7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid (0.99 g, 3.6 mmol) and triethylamine (0.36 g, 3.6 mmol) in dry DMF (10 mL) was added in dropwise a solution of diphenylphosphoryl azide (0.99 g, 3.6 mmol), in DMF (5 mL) over a period of 2 h. After removal of the cooling bath, the mixture was stirred at room temperature for 12 h. It was poured into ice and the precipitate therefore formed was collected by vacuum filtration, which appeared to be the title compound (0.10 g). Extract the rest part of the mixture with ethyl acetate (20 mL×2). The organic layers were combined, washed with saturated aqueous NaHCO3, brine, and dried over anhydrous Na2SO4. It was concentrated and the oil obtained was treated with diethyl ether to give additional title compound as a solid precipitate (0.23 g).

Provenance & Evidence