Azido(trimethyl)stannane → 2-Butyl-3-{5-[2-(1H-tetrazol-5-yl)-phenyl]-indan-1-yl}-1,3-diaza-spiro[4.4]non-1-en-4-one

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Reaction Steps

A mixture of 2-[1-(2-butyl-4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-yl)-indan -5yl]-benzonitrile (150 mg, 0.36 mmol) and trimethyltin azide (196 mg, 0.91 mmol) was heated under reflux in xylene (5.0 mL) for 25 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was chromatographed on SiO2 -gel using a gradient of 2.5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2 to give 51 mg of a colorless oil. The oil was dissolved in EtOAc and hexanes were added to precipitate the product. The white solid was filtered and dried. 1H NMR (250 MHz, d4 -MeOH): d 7.58 (m, 2 H), 7.47 (m, 2 H), 7.00 (s, 1 H), 6.85 (s, 2 H), 5.50 (t, 1 H), 2.95 (m, 2 H), 2.35 (m, 4 H), 1.90-1.41 (m), 1.22 (m, 2 H), 0.80 (t, 3 H).

Provenance & Evidence