Tert-Butyl nitrite → 2-Azido-8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Participants

Reaction Conditions

Reaction Steps

To a suspension of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-ylamine (2.38 g, 8 mmol) in acetonitrile at 0° C. was added tert-butyl nitrite (1.43 mL, 12 mmol) followed by trimethylsilyl azide (1.26 mL, 9.6 mmol) dropwise. The reaction mixture was stirred at 0° C. for 90 mins, allowed to warm up to RT and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, 10% ethyl acetate in cyclohexane) to yield the title compound as a red oil which solidified upon standing (956 mg, 37%). 1H NMR (CDCl3): 8.21 (1 H, d, J=8.6 Hz), 7.24 (1 H, dd, J=8.6, 2.1 Hz), 7.20 (1 H, d, J=2.1 Hz), 4.34 (2 H, t, J=5.1 Hz), 3.21 (2 H, t, J=5.1 Hz).

Provenance & Evidence